| Identifier | 1 |
|---|---|
| Cyclic voltammetry, potential | E₁/₂ = −2.60 V vs. SCE |
| Cyclic voltammetry, conditions | CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆ in CH₃CN; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN |
Yihang Li, Jenny Hui Foong Chau, Yan Wang, Chunli Xie, Jia Wang, Liangtao Xie, Wei Lu, Chao Zou, Yuliang Liu, Haoyu Li. “Transient polarity amplification enables Markovnikov hydroamination with free alkyl amines.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15007663/v1
Photoreaction quantum-yield results were not retained
| Cyclic voltammetry, potential | Eₚ/₂ = −2.81 V vs. SCE |
|---|---|
| Cyclic voltammetry, conditions | CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆ in CH₃CN; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN |
| Identifier | PAZ |
|---|---|
| Cyclic voltammetry, ground-state redox oxidation potential | +0.18 V vs SCE |
| Cyclic voltammetry, graphical potential annotations | +0.23 V, +0.12 V, +1.08 V, +0.94 V vs SCE |
| Cyclic voltammetry, conditions | Conditions stated for Figs. S3–S7: alkene substrates (5 mM) and n-Bu₄NPF₆ (0.1 M) in CH₃CN; CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN |
| Normalized absorption and emission spectra, intersection | 417 nm (2.97 eV) |
| α-Methylstyrene identifier | 1 |
|---|---|
| Stern–Volmer fluorescence quenching | α-Methylstyrene quenched the excited state of PAZ; y = 0.0137x + 1, R² = 0.999 |
| Stern–Volmer fluorescence quenching, conditions | PAZ (0.5 mM) in CH₃CN in a 3.5 mL quartz cuvette; excitation at 365 nm; emission intensity at 465 nm; baseline and quencher concentrations of 12.5, 25, 37.5, 50, and 62.5 mM |
| EPR reported in Main (415 nm, 10 min) | Clear EPR signal; isotropic g = 2.001; assigned to PAZ˙⁺ |
| EPR reported in SI (415 nm, 5 min) | No signal in the dark; after irradiation, g = 2.001 and AN = 0.632 mT; assigned to the PAZ radical cation |
| EPR reported in SI, sample | 1 (0.4 mmol), PAZ (0.004 mmol), and CH₃CN (1.0 mL); 20 μL aliquot in a capillary tube inside an EPR tube |
| n-Butylamine identifier | 2 |
|---|---|
| Stern–Volmer fluorescence quenching | No measurable quenching; y = −0.000113x + 1, R² = 0.999 |
| Stern–Volmer fluorescence quenching, conditions | PAZ (0.5 mM) in CH₃CN in a 3.5 mL quartz cuvette; excitation at 365 nm; emission intensity at 465 nm; baseline and quencher concentrations of 12.5, 25, 37.5, 50, and 62.5 mM |
| EPR reported in Main | Irradiated PAZ and 2 remained EPR-silent |
| EPR reported in SI (415 nm irradiation) | No EPR signal was observed |
| EPR reported in SI, sample | CH₃CN solution (0.4 M) containing PAZ (0.004 mmol) and 2 (0.6 mmol) |
| Identifier | s1 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.80 (d, J = 8.0 Hz, 1H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 7.15 (d, J = 7.5 Hz, 2H), 4.85 (ddd, J = 8.0, 6.5, 6.5 Hz, 1H), 3.72 (s, 3H), 3.70 – 3.66 (m, 1H), 3.69 (s, 3H), 3.15 (dd, J = 14.0, 6.0 Hz, 1H), 3.09 (dd, J = 14.0, 6.0 Hz, 1H), 2.84 (dd, J = 16.5, 3.5 Hz, 1H), 2.55 (dd, J = 12.0, 3.5 Hz, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 172.9, 172.2, 171.8, 135.9, 129.2, 128.5, 127.0, 52.9, 52.2, 51.8, 51.8, 39.0, 38.0 |
| Identifier | s2 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.40 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 5.35 (s, 1H), 5.06 – 5.04 (m, 1H), 2.49 (s, 3H), 2.13 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 142.5, 138.0, 137.5, 126.4, 125.9, 111.9, 21.7, 15.9 |
| Identifier | s3 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.42 (d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.5 Hz, 2H), 5.35 (s, 1H), 5.05 – 5.02 (m, 1H), 2.14 (s, 3H), 1.32 (s, 9H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 150.4, 142.9, 138.3, 125.2, 125.1, 111.7, 34.5, 31.3, 21.8 |
| Identifier | s4 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.60 (d, J = 8.5 Hz, 2H), 7.58 – 7.54 (m, 4H), 7.44 (dd, J = 7.5, 7.5 Hz, 2H), 7.34 (t, J = 7.5 Hz, 1H), 5.43 (s, 1H), 5.11 (d, J = 1.5 Hz, 1H), 2.19 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 142.8, 140.8, 140.2, 140.1, 128.8, 127.3, 127.0, 126.9, 125.9, 112.5, 21.8 |
| Identifier | s5 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.77 (d, J = 8.0 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 5.41 (s, 1H), 5.12 (s, 1H), 2.16 (s, 3H), 1.35 (s, 12H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 144.0, 143.3, 134.7, 124.8, 113.2, 83.7, 24.8, 21.7 |
| ¹³C NMR reporting qualifier | The boron-bound carbon was not detected |
| Identifier | s6 |
|---|---|
| Cyclic voltammetry, potential | Eₚ/₂ = −2.94 V vs. SCE |
| Cyclic voltammetry, conditions | CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; CH₃CN; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN |
| ¹H NMR (500 MHz, CDCl₃) | δ 6.98 (d, J = 1.5 Hz, 1H), 6.94 (dd, J = 8.0, 1.5 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 5.94 (s, 2H), 5.22 (s, 1H), 5.00 – 4.97 (m, 1H), 2.10 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.6, 147.0, 142.7, 135.6, 119.1, 111.3, 107.9, 106.0, 101.0, 22.1 |
| Identifier | s7 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 6.61 (d, J = 2.0 Hz, 2H), 6.40 (t, J = 2.0 Hz, 1H), 5.35 (s, 1H), 5.08 (s, 1H), 3.80 (s, 6H), 2.12 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 160.6, 143.5, 143.3, 112.8, 104.0, 99.3, 55.3, 21.9 |
| Identifier | s8 |
|---|---|
| Cyclic voltammetry, potential | Eₚ/₂ = −2.93 V vs. SCE |
| Cyclic voltammetry, conditions | CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; DMSO; Fc internal reference, E(Fc⁺/Fc) = 435 mV in DMSO |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.39 (d, J = 9.0 Hz, 2H), 6.70 (d, J = 9.0 Hz, 2H), 5.25 (s, 1H), 4.91 – 4.89 (m, 1H), 2.95 (s, 6H), 2.12 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 150.0, 142.7, 129.3, 126.2, 112.1, 108.8, 40.6, 21.8 |
| Identifier | s9 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.53 (d, J = 7.5 Hz, 1H), 7.44 (dd, J = 8.5, 1.0 Hz, 1H), 7.26 (ddd, J = 7.0, 7.0, 1.0 Hz, 2H), 7.19(td, J = 7.0, 7.0, 1.0 Hz, 1H), 6.64 (s, 1H), 5.79 (s, 1H), 5.19 – 5.16 (m, 1H), 2.13 (dd, J = 1.5, 1.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 156.9, 154.8, 132.8, 129.0, 124.5, 122.6, 120.9, 113.2, 111.0, 102.8, 19.4 |
| Identifier | s10 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 8.25 (d, J = 2.5 Hz, 1H), 7.69 (dd, J = 8.5, 2.5 Hz, 1H), 6.71 (d, J = 8.5 Hz, 1H), 5.30 (s, 1H), 5.07 – 5.01 (m, 1H), 3.94 (s, 3H), 2.13 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 163.5, 143.8, 140.1, 135.8, 129.9, 111.8, 110.3, 53.4, 21.6 |
| Identifier | s11 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 8.00 (d, J = 8.5 Hz, 2H), 7.41 (d, J = 8.5 Hz, 2H), 7.24 (d, J = 8.5 Hz, 2H), 6.87 (d, J = 8.5 Hz, 2H), 5.48 (s, 1H), 5.43 (s, 1H), 3.93 (s, 3H), 3.83 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 167.0, 159.5, 148.7, 146.4, 133.3, 129.5, 129.3, 129.3, 128.3, 114.5, 113.7, 55.3, 52.1 |
| Identifier | s12 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.46 – 7.41 (m, 2H), 7.39 – 7.33 (m, 3H), 7.23 (dd, J = 5.5, 1.0 Hz, 1H), 6.98 (dd, J = 5.5, 3.5 Hz, 1H), 6.91 (dd, J = 3.5, 1.0 Hz, 1H), 5.58 (d, J = 1.0 Hz, 1H), 5.24 (d, J = 1.0 Hz, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 144.8, 143.4, 141.0, 128.3, 128.2, 128.0, 127.3, 126.5, 125.0, 113.6 |
| Identifier | s13 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 (d, J = 7.5 Hz, 2H), 7.21 – 7.15 (m, 4H), 7.11 (d, J = 7.5 Hz, 2H), 5.42 – 5.40 (m, 2H), 3.14 (s, 4H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 151.9, 141.2, 138.4, 128.9, 128.2, 127.7, 126.2, 117.5, 33.3 |
| Identifier | s14 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.65 (d, J = 7.0 Hz, 1H), 7.19 – 7.13 (m, 2H), 7.10 (d, J = 7.0 Hz, 1H), 5.48 (s, 1H), 4.96 (s, 1H), 2.85 (t, J = 6.5 Hz, 2H), 2.55 (t, J = 6.5 Hz, 2H), 1.92 – 1.85 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 143.4, 137.3, 134.7, 129.2, 127.6, 125.9, 124.2, 107.8, 33.2, 30.4, 23.8 |
| Identifier | s15 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.41 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.26 (t, J = 7.5 Hz, 1H), 5.26 (s, 1H), 5.05 (s, 1H), 2.50 (t, J = 7.5 Hz, 2H), 1.47 – 1.39 (m, 2H), 1.39 – 1.30 (m, 2H), 0.89 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.7, 141.4, 128.2, 127.2, 126.1, 112.0, 35.0, 30.4, 22.4, 13.9 |
| Identifier | s16 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.59 (d, J = 7.0 Hz, 2H), 7.34 (dd, J = 7.0, 7.0 Hz, 2H), 7.28 (t, J = 7.0 Hz, 1H), 5.27 (s, 1H), 4.93 (s, 1H), 1.68 – 1.62 (m, 1H), 0.86 – 0.82 (m, 2H), 0.61 – 0.58 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.4, 141.6, 128.1, 127.4, 126.1, 109.0, 15.6, 6.7 |
| Identifier | s17 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 – 7.23 (m, 5H), 5.13 (d, J = 1.5 Hz, 1H), 5.00 (dd, J = 1.5, 1.5 Hz, 1H), 2.42 (tt, J = 11.5, 3.0 Hz, 1H), 1.87 – 1.81 (m, 2H), 1.78 (dt, J = 13.0, 3.5 Hz, 2H), 1.73 – 1.68 (m, 1H), 1.37 – 1.27 (m, 2H), 1.23 – 1.10 (m, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 155.0, 143.0, 128.1, 127.0, 126.6, 110.3, 42.6, 32.7, 26.8, 26.4 |
| Identifier | s18 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.38 (d, J = 9.0 Hz, 2H), 6.84 (d, J = 9.0 Hz, 2H), 5.37 – 5.34 (m, 1H), 5.27 – 5.25 (m, 1H), 3.82 (s, 3H), 1.98 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 159.4, 133.0, 127.0, 121.2, 115.3, 113.9, 89.2, 88.3, 55.2, 23.6 |
| Identifier | s19 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.29 – 7.26 (m, 2H), 7.20 (s, 1H), 5.33 (s, 1H), 5.04 (s, 1H), 2.93 (dd, J = 9.0, 4.0 Hz, 2H), 2.51 (dd, J = 19.0, 8.5 Hz, 1H), 2.46 – 2.41 (m, 1H), 2.31 (ddd, J = 10.5, 10.5, 3.5 Hz, 1H), 2.19 – 2.10 (m, 1H), 2.13 (s, 3H), 2.10 – 2.00 (m, 2H), 1.99 – 1.94 (m, 2H), 1.68 – 1.41 (m, 6H), 0.91 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 221.0, 142.9, 139.0, 138.7, 136.2, 126.1, 125.2, 122.9, 111.8, 50.4, 47.9, 44.3, 38.1, 35.8, 31.5, 29.5, 26.5, 25.6, 21.8, 21.5, 13.8 |
| Identifier | s20 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.63 (d, J = 16.0 Hz, 1H), 7.11 (dd, J = 8.0, 2.0 Hz, 1H), 7.06 (d, J = 2.0 Hz, 1H), 6.87 (d, J = 8.0 Hz, 1H), 6.31 (d, J = 16.0 Hz, 1H), 4.26 (q, J = 7.0 Hz, 2H), 3.92 (s, 3H), 3.92 (s, 3H), 1.34 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 167.2, 151.1, 149.2, 144.5, 127.5, 122.6, 116.0, 111.0, 109.6, 60.4, 56.0, 55.9, 14.4 |
| Identifier | s21 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 (s, 2H), 5.82 (d, J = 7.5 Hz, 1H), 4.38 – 4.30 (m, 1H), 3.77 (dd, J = 9.0, 4.0 Hz, 1H), 3.67 (dd, J = 9.0, 3.0 Hz, 1H), 2.21 (s, 6H), 2.02 (s, 3H), 1.39 (d, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 169.4, 154.9, 137.6, 133.3, 87.9, 73.9, 45.3, 23.4, 17.6, 15.7 |
| HRMS (ESI) | m/z calcd for C₁₃H₁₉NIO₂ [M + H]⁺ 348.0455; found 348.0453 |
| IR (ATR) νmax | 3278, 3101, 2970, 1647, 1562, 1471, 1372, 1202, 869 cm⁻¹ |
| Identifier | s22 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.12 (s, 2H), 5.94 (br s, 1H), 5.28 (s, 1H), 5.01 (s, 1H), 4.39 – 4.30 (m, 1H), 3.80 (dd, J = 9.0, 4.0 Hz, 1H), 3.70 (dd, J = 9.0, 3.0 Hz, 1H), 2.26 (s, 6H), 2.11 (s, 3H), 2.04 (s, 3H), 1.41 (d, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 169.4, 154.3, 142.7, 137.0, 130.3, 126.2, 111.7, 73.9, 45.3, 23.5, 21.9, 17.7, 16.3 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₄NO₂ [M + H]⁺ 262.1802; found 262.1801 |
| IR (ATR) νmax | 3273, 3089, 2987, 1648, 1611, 1472, 1367, 1196, 762 cm⁻¹ |
| Identifier | s23 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.35 – 7.31 (m, 5H), 7.30 – 7.24 (m, 3H), 7.22 (ddd, J = 7.0, 1.5, 1.5 Hz, 1H), 5.47 (s, 1H), 5.46 (s, 1H), 3.71 (q, J = 7.0 Hz, 1H), 3.66 (s, 3H), 1.49 (d, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 174.9, 149.8, 141.8, 141.3, 140.5, 128.4, 128.2, 128.2, 127.8, 127.5, 127.2, 126.7, 114.5, 52.0, 45.3, 18.6 |
| Identifier | s24 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.27 (s, 1H), 6.85 (dd, J = 16.5, 11.0 Hz, 1H), 6.55 (s, 1H), 5.52 (d, J = 16.5 Hz, 1H), 5.14 (d, J = 11.0 Hz, 1H), 3.92 (t, J = 5.5 Hz, 2H), 3.66 (s, 3H), 2.31 (s, 3H), 2.19 (s, 3H), 1.77 – 1.68 (m, 4H), 1.22 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 178.2, 156.6, 134.2, 133.9, 128.5, 127.5, 124.3, 112.7, 112.5, 68.0, 51.7, 42.0, 37.0, 25.1, 25.1, 19.6, 15.7 |
| HRMS (ESI) | m/z calcd for C₁₈H₂₇O₃ [M + H]⁺ 291.1955; found 291.1954 |
| IR (ATR) νmax | 3086, 2973, 1724, 1609. 1504, 1396, 1260, 1194, 899 cm⁻¹ |
| Identifier | 3 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.42 (dd, J = 8.5, 1.5 Hz, 2H), 7.33 (dd, J = 8.5, 8.5 Hz, 2H), 7.21 (tt, J = 8.5, 1.5 Hz, 1H), 2.30 (t, J = 7.0 Hz, 2H), 1.49 (br s, 1H), 1.45 (s, 6H), 1.43 – 1.36 (m, 2H), 1.33 – 1.24 (m, 2H), 0.85 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.0, 128.1, 126.1, 125.6, 55.7, 42.7, 33.1, 29.6, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₂N [M + H]⁺ 192.1747; found 192.1746 |
| IR (ATR) νmax | 3322, 3085, 2958, 1601, 1494, 1378, 1181, 763, 698 cm⁻¹ |
| Identifier | 4 |
|---|---|
| ¹H NMR (500 MHz, DMSO-d₆) | δ 7.54 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.31 – 7.25 (m, 4H), 7.22 – 7.16 (m, 2H), 3.35 (s, 2H), 1.43 (s, 3H), 1.42 – 1.37 (m, 2H) |
| ¹³C NMR (125 MHz, DMSO-d₆) | δ 148.2, 141.7, 128.03, 127.99, 127.86, 126.3, 126.0, 125.8, 55.7 (t, JC-D = 7.5 Hz), 47.9, 29.5, 29.1 (t, JC-D = 18.8 Hz) |
| HRMS (ESI) | m/z calcd for C₁₆H₁₈D₂N [M + H]⁺ 228.1716; found 228.1715 |
| IR (ATR) νmax | 3326, 3084, 2967, 2050, 1600, 1493, 1379, 1182, 763, 697 cm⁻¹ |
| Deuterium labeling, D/H at the newly formed C–H bond | >95 % |
| Deuterium labeling, conditions | 1 (0.4 mmol), BnND₂ (1.5 equiv), PAZ (1 mol%), CH₃CN, 415 nm LEDs, 12 h |
| Identifier | 5 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.53 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.32 – 7.27 (m, 4H), 7.26 – 7.19 (m, 2H), 3.48 (s, 2H), 1.57 (br s, 1H), 1.53 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.7, 141.2, 128.3, 128.2, 128.2, 126.7, 126.3, 125.9, 56.1, 47.6, 29.7 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1590 |
| IR (ATR) νmax | 3326, 3085, 2670, 1600, 1494, 1379, 1183, 763, 697 cm⁻¹ |
| Identifier | 6 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.42 (d, J = 8.0 Hz, 2H), 7.32 (dd, J = 8.0, 8.0 Hz, 2H), 7.21 (t, J = 8.0 Hz, 1H), 2.15 (d, J = 7.0 Hz, 2H), 1.59 (br s, 1H), 1.47 (s, 6H), 0.95 – 0.84 (m, 1H), 0.45 – 0.40 (m, 2H), 0.01 – -0.03 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.7, 128.1, 126.1, 125.6, 55.5, 48.3, 29.5, 11.7, 3.3 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1589 |
| IR (ATR) νmax | 3327, 3081, 2957, 1600, 1491, 1376, 1143, 762, 700 cm⁻¹ |
| Identifier | 7 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.43 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 2.24 (d, J = 7.0 Hz, 2H), 1.95 – 1.85 (m, 1H), 1.79 – 1.69 (m, 2H), 1.56 – 1.46 (m, 4H), 1.45 (s, 6H), 1.11 – 1.01 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.1, 128.1, 126.0, 125.8, 55.6, 48.7, 40.7, 30.9, 29.6, 25.2 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1903 |
| IR (ATR) νmax | 3326, 3085, 2864, 1601, 1494, 1378, 1182, 763, 698 cm⁻¹ |
| Identifier | 8 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 3.45 (t, J = 5.5 Hz, 2H), 3.32 (s, 3H), 2.50 (t, J = 5.5 Hz, 2H), 1.81 (br s, 1H), 1.47 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.6, 128.1, 126.1, 125.7, 72.7, 58.6, 55.5, 42.4, 29.6 |
| HRMS (ESI) | m/z calcd for C₁₂H₂₀NO [M + H]⁺ 194.1540; found 194.1539 |
| IR (ATR) νmax | 3330, 3077, 2972, 1602, 1494, 1377, 1235, 1180, 763, 698 cm⁻¹ |
| Identifier | 9 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 4.54 (t, J = 5.5 Hz, 1H), 3.62 (dq, J = 9.5, 7.0 Hz, 2H), 3.48 (dq, J = 9.5, 7.0 Hz, 2H), 2.48 (d, J = 5.5 Hz, 2H), 1.66 (br s, 1H), 1.46 (s, 6H), 1.19 (t, J = 7.5 Hz, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.6, 128.1, 126.1, 125.7, 102.8, 62.1, 55.3, 45.6, 29.5, 15.3 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₆NO₂ [M + H]⁺ 252.1958; found 252.1956 |
| IR (ATR) νmax | 3332, 3086, 2928, 1601, 1494, 1378, 1180, 1061, 764, 699 cm⁻¹ |
| Identifier | 10 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.45 (d, J = 7.5 Hz, 2H), 7.35 (dd, J = 7.5, 7.5 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 2.92 – 2.83 (m, 2H), 1.56 (br s, 1H), 1.48 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.3, 128.4, 126.7, 125.8, 125.7 (q, JC-F = 272.5 Hz), 55.8, 45.3 (q, JC-F = 31.3 Hz), 29.6 |
| ¹⁹F NMR (470 MHz, CDCl₃) | δ −72.2 (t, JH-F = 9.4 Hz) |
| HRMS (ESI) | m/z calcd for C₁₁H₁₅NF₃ [M + H]⁺ 218.1151; found 218.1151 |
| IR (ATR) νmax | 3350, 3089, 2971, 1602, 1496, 1267, 1186, 765, 699 cm⁻¹ |
| Identifier | 11 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.46 (d, J = 7.5 Hz, 2H), 7.34 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 2.62 (t, J = 6.5 Hz, 2H), 2.40 (t, J = 6.5 Hz, 2H), 1.57 (br s, 1H), 1.48 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.9, 128.3, 126.5, 125.7, 118.9, 56.0, 39.0, 29.6, 19.7 |
| HRMS (ESI) | m/z calcd for C₁₂H₁₇N₂ [M + H]⁺ 189.1386; found 189.1386 |
| IR (ATR) νmax | 3321, 3086, 2971, 2248, 1601, 1495, 1372, 1183, 766, 701 cm⁻¹ |
| Identifier | 12 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (dd, J = 7.5, 1.0 Hz, 2H), 7.35 (dd, J = 7.5, 7.5 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 3.12 (t, J = 6.0 Hz, 2H), 2.94 (s, 3H), 2.85 (t, J = 6.0 Hz, 2H), 1.94 (br s, 1H), 1.50 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.4, 128.4, 126.7, 125.7, 56.4, 55.7, 42.0, 37.1, 29.1 |
| HRMS (ESI) | m/z calcd for C₁₂H₂₀NO₂S [M + H]⁺ 242.1209; found 242.1209 |
| IR (ATR) νmax | 3377, 3015, 2928, 1600, 1270, 1116, 764, 703 cm⁻¹ |
| Identifier | 13 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.49 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5, 1H), 2.28 (p, J = 6.0 Hz, 1H), 1.47 (s, 6H), 1.28 – 1.20 (m, 4H), 0.74 (t, J = 7.5 Hz, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.9, 127.8, 126.1, 126.0, 55.6, 54.4, 29.9, 27.9, 9.8 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₄N [M + H]⁺ 206.1903; found 206.1903 |
| IR (ATR) νmax | 3349, 3086, 2962, 1601, 1493, 1379, 1177, 762, 698 cm⁻¹ |
| Identifier | 14 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 3.09 – 3.02 (m, 1H), 2.08 – 1.99 (m, 2H), 1.71 – 1.60 (m, 2H), 1.59 – 1.49 (m, 2H), 1.42 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.4, 128.0, 126.1, 125.8, 56.0, 49.8, 34.2, 30.3, 15.1 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1590 |
| IR (ATR) νmax | 3321, 3085, 2963, 1601, 1494, 1378, 1183, 763, 698 cm⁻¹ |
| Identifier | 15 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5 Hz, 2H), 7.21 (dd, J = 7.5 Hz, 1H), 2.79 – 2.72 (m, 2H), 1.73 – 1.67 (m, 2H), 1.64 – 1.56 (m, 2H), 1.45 (s, 6H), 1.41 – 1.32 (m, 2H), 1.26 – 1.16 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.9, 128.0, 126.1, 125.8, 56.2, 55.3, 35.7, 30.5, 23.9 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₂N [M + H]⁺ 204.1747; found 204.1747 |
| IR (ATR) νmax | 3325, 3085, 2955, 1601, 1494, 1373, 1182, 764, 699 cm⁻¹ |
| Identifier | 16 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.46 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 2.25 – 2.18 (m, 1H), 1.64 – 1.55 (m, 4H), 1.64 – 1.55 (m, 1H), 1.46 (s, 6H), 1.15 – 0.96 (m, 5H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.9, 127.8, 126.0, 125.9, 56.0, 52.0, 36.4, 30.4, 25.7, 25.5 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1903 |
| IR (ATR) νmax | 3329, 3086, 2923, 1601, 1494, 1378, 1180, 763, 698 cm⁻¹ |
| Identifier | 17 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.47 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 3.81 (dt, J = 11.5, 3.0 Hz, 2H), 3.23 (td, J = 11.5, 2.0 Hz, 2H), 2.48 (tt, J = 10.5, 4.5 Hz, 1H), 1.54 – 1.48 (m, 3H), 1.47 (s, 6H), 1.41 – 1.32 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.6, 128.0, 126.3, 125.9, 67.1, 56.0, 49.3, 36.4, 30.5 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₂NO [M + H]⁺ 220.1696; found 220.1695 |
| IR (ATR) νmax | 3308, 3086, 2938, 1601, 1494, 1379, 1235, 1168, 771 cm⁻¹ |
| Single-crystal XRD, identification code | z2 |
| Single-crystal XRD, empirical formula | C₁₄H₂₁NO |
| Single-crystal XRD, formula weight | 219.32 |
| Single-crystal XRD, temperature/K | 100.0 |
| Single-crystal XRD, crystal system | monoclinic |
| Single-crystal XRD, space group | P2₁ |
| Single-crystal XRD, a/Å | 7.4671(5) |
| Single-crystal XRD, b/Å | 11.8631(9) |
| Single-crystal XRD, c/Å | 7.7175(5) |
| Single-crystal XRD, α/° | 90 |
| Single-crystal XRD, β/° | 112.218(3) |
| Single-crystal XRD, γ/° | 90 |
| Single-crystal XRD, volume/ų | 632.88(8) |
| Single-crystal XRD, Z | 2 |
| Single-crystal XRD, ρcalc g/cm³ | 1.151 |
| Single-crystal XRD, μ/mm⁻¹ | 0.071 |
| Single-crystal XRD, F(000) | 240.0 |
| Single-crystal XRD, crystal size/mm³ | 0.21 × 0.19 × 0.17 |
| Single-crystal XRD, radiation | MoKα (λ = 0.71073) |
| Single-crystal XRD, 2Θ range for data collection/° | 5.702 to 55.118 |
| Single-crystal XRD, index ranges | −9 ≤ h ≤ 9, −15 ≤ k ≤ 15, −10 ≤ l ≤ 10 |
| Single-crystal XRD, reflections collected | 18121 |
| Single-crystal XRD, independent reflections | 2896 [Rint = 0.0870, Rsigma = 0.0552] |
| Single-crystal XRD, data/restraints/parameters | 2896/3/152 |
| Single-crystal XRD, goodness-of-fit on F² | 1.072 |
| Single-crystal XRD, final R indexes [I ≥ 2σ(I)] | R1 = 0.0399, wR2 = 0.0834 |
| Single-crystal XRD, final R indexes [all data] | R1 = 0.0507, wR2 = 0.0928 |
| Single-crystal XRD, largest diff. peak/hole / e Å⁻³ | 0.15/−0.17 |
| Single-crystal XRD, Flack parameter | −0.5(19) |
| Single-crystal XRD, CCDC deposition number | 2577572 |
| Identifier | 18 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.51 (d, J = 7.5 Hz, 2H), 7.27 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 1.54 (br s, 1H), 1.51 (s, 6H), 0.96 (s, 9H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 151.1, 127.6, 125.8, 125.7, 55.5, 51.8, 32.8, 32.6 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₂N [M + H]⁺ 192.1747; found 192.1746 |
| IR (ATR) νmax | 3346, 3085, 2968, 1601, 1493, 1376, 1181, 764, 698 cm⁻¹ |
| Identifier | 19 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.52 (d, J = 7.5 Hz, 2H), 7.27 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 1.90 – 1.85 (m, 3H), 1.61 (br s, 1H), 1.54 – 1.44 (m, 12H), 1.52 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 151.4, 127.6, 125.8, 125.7, 55.4, 52.6, 45.7, 36.5, 33.4, 29.9 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₈N [M + H]⁺ 270.2216; found 270.2215 |
| IR (ATR) νmax | 3338, 3083, 2898, 1600, 1493, 1379, 1184, 771, 703 cm⁻¹ |
| Identifier | 20 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.69 (d, J = 8.0 Hz, 2H), 7.33 (dd, J = 8.0, 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 7.28 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 7.19 (t, J = 8.0 Hz, 1H), 3.39 (s, 2H), 2.12 (s, 3H), 1.44 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.7, 141.2, 128.3, 128.1, 128.0, 126.4, 126.2, 126.2, 60.3, 55.7, 34.5, 24.0 |
| HRMS (ESI) | m/z calcd for C₁₇H₂₂N [M + H]⁺ 240.1747; found 240.1747 |
| IR (ATR) νmax | 3086, 2904, 1602, 1493, 1178, 764, 698 cm⁻¹ |
| Identifier | 21 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.55 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5, 1H), 5.76 (ddt, J = 16.5, 10.0, 6.0 Hz, 1H), 5.11 (d, J = 16.5 Hz, 1H), 5.02 (d, J = 10.0 Hz, 1H), 2.83 (d, J = 6.0 Hz, 2H), 2.21 (s, 3H), 1.35 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.7, 137.9, 127.9, 126.1, 126.0, 115.7, 60.2, 54.8, 34.3, 24.0 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1590 |
| IR (ATR) νmax | 3083, 2972, 1642, 1600, 1492, 1377, 1181, 913, 764, 698 cm⁻¹ |
| Identifier | 22 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.53 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 3.15 (d, J = 2.5 Hz, 2H), 2.40 (s, 3H), 2.16 (t, J = 2.5 Hz, 1H), 1.39 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.7, 128.1, 126.4, 126.0, 82.5, 71.4, 60.3, 41.0, 34.9, 24.2 |
| HRMS (ESI) | m/z calcd for C₁₃H₁₈N [M + H]⁺ 188.1434; found 188.1433 |
| IR (ATR) νmax | 3303, 3087, 2972, 1600, 1494, 1376, 1181, 759, 699 cm⁻¹ |
| Identifier | 23 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.26 (d, J = 8.0 Hz, 2H), 6.84 (d, J = 8.0 Hz, 2H), 3.80 (s, 3H), 3.79 (q, J = 7.0 Hz, 1H), 2.46 – 2.38 (m, 2H), 2.36 – 2.28 (m, 2H), 1.43 – 1.33 (m, 4H), 1.29 (d, J = 7.0 Hz, 3H), 1.27 – 1.20 (m, 4H), 0.86 (t, J = 7.5 Hz, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.1, 136.9, 128.7, 113.2, 58.1, 55.2, 49.5, 30.0, 20.6, 16.5, 14.1 |
| HRMS (ESI) | m/z calcd for C₁₄H₃₀NO [M + H]⁺ 264.2322; found 264.2322 |
| IR (ATR) νmax | 3061, 2955, 1610, 1509, 1376, 1243, 1174, 831 cm⁻¹ |
| Identifier | 24 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.49 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.26 (t, J = 7.5 Hz, 1H), 3.28 (t, J = 6.5 Hz, 4H), 2.02 – 1.93 (m, 2H), 1.43 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 128.2, 127.0, 126.6 (Overlapped with 2C), 58.4, 47.4, 23.3, 15.7 |
| HRMS (ESI) | m/z calcd for C₁₂H₁₈N [M + H]⁺ 176.1434; found 176.1433 |
| IR (ATR) νmax | 3087, 2966, 1599, 1493, 1377, 1180, 793, 699 cm⁻¹ |
| Identifier | 25 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.51 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 2.55 – 2.49 (m, 4H), 1.72 – 1.67 (m, 4H), 1.42 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.9, 127.8, 126.3, 126.0, 57.5, 46.1, 24.6, 23.8 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1591 |
| IR (ATR) νmax | 3083, 2968, 1599, 1491, 1379, 1178, 763, 698 cm⁻¹ |
| Identifier | 26 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.56 (d, J = 7.5 Hz, 2H), 7.49 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 7.17 (t, J = 7.5 Hz, 1H), 4.22 (dd, J = 9.0, 3.5 Hz, 1H), 2.82 (ddd, J = 9.0, 6.5, 3.5 Hz, 1H), 2.59 (ddd, J = 9.0, 9.0, 6.5 Hz, 1H), 2.17 – 2.07 (m, 1H), 1.81 – 1.74 (m, 1H), 1.66 – 1.56 (m, 2H), 1.44 (s, 3H), 1.11 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 150.7, 149.5, 127.9, 127.8, 126.4, 126.4, 125.9, 125.8, 61.2, 59.5, 49.6, 37.7, 31.9, 24.5, 19.1 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₄N [M + H]⁺ 266.1903; found 266.1902 |
| IR (ATR) νmax | 3083, 2967, 1600, 1490, 1381, 1185, 764, 697 cm⁻¹ |
| Identifier | 27 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.51 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 4.92 (br s, 1H), 3.71 – 3.63 (m, 1H), 2.96 – 2.88 (m, 1H), 2.62 (d, J = 8.0 Hz, 1H), 2.60 – 2.50 (m, 1H), 2.41 (d, J = 8.0 Hz, 1H), 1.43 (s, 9H), 1.39 (s, 3H), 1.38 (s, 3H), 0.77 – 0.67 (m, 2H), 0.54 – 0.48 (m, 1H), 0.43 – 0.37 (m, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 155.7, 147.6, 127.9, 126.3, 126.0, 79.0, 57.3, 56.0, 54.2, 54.1, 31.7, 28.4, 26.3, 24.3, 24.2, 14.2, 8.3 |
| HRMS (ESI) | m/z calcd for C₂₀H₃₁N₂O₂ [M + H]⁺ 331.2380; found 331.2378 |
| IR (ATR) νmax | 3349, 3059, 2075, 1702, 1492, 1390, 1164, 765, 700 cm⁻¹ |
| Identifier | 28 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.52 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 3.99 (m, 1H), 2.80 – 2.72 (m, 2H), 2.29 – 2.21 (m, 2H), 2.08 – 2.01 (m, 2H), 1.89 – 1.81 (m, 2H), 1.33 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.5, 128.0, 126.1, 125.8, 59.9, 58.6, 44.6, 36.7, 24.3 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₁NCl [M + H]⁺ 238.1357; found 238.1357 |
| IR (ATR) νmax | 3084, 2968, 1598, 1491, 1376, 1174, 764, 699 cm⁻¹ |
| Identifier | 29 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.53 (d, J = 8.0, 2H), 7.30 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 4.68 – 4.56 (m, 1H), 2.67 – 2.62 (m, 2H), 2.37 – 2.33 (m, 2H), 1.92 – 1.75 (m, 4H), 1.34 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.6, 128.0, 126.1, 125.8, 89.7(d, JC-F = 170.0 Hz), 59.9, 42.6 (d, JC-F = 6.3 Hz), 32.6 (d, JC-F = 18.8 Hz), 24.3 |
| ¹⁹F NMR (470 MHz, CDCl₃) | δ −178.5 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₁NF [M + H]⁺ 222.1653; found 222.1652 |
| IR (ATR) νmax | 3085, 2971, 1601, 1492, 1367, 1178, 1029, 762, 699 cm⁻¹ |
| Identifier | 30 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.53 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 4.5 Hz, 1H), 3.67 (t, J = 7.5 Hz, 4H), 2.47 (t, J = 7.5 Hz, 4H), 1.34 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.7, 128.0, 126.20, 126.19, 67.9, 59.6, 46.6, 23.8 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₀NO [M + H]⁺ 206.1540; found 206.1538 |
| IR (ATR) νmax | 3063, 2851, 1610, 1510, 1371, 1240, 1177, 1116, 738 cm⁻¹ |
| Identifier | 31 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.50 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 2.77 – 2.75 (m, 4H), 2.64 – 2.62 (m, 4H), 1.32 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.5, 128.0, 126.1, 126.0, 60.8, 49.0, 29.0, 24.3 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₀NS [M + H]⁺ 222.1311; found 222.1312 |
| IR (ATR) νmax | 3084, 2972, 1598, 1491, 1372, 1171, 732, 699 cm⁻¹ |
| Identifier | 32 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.60 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 7.12 – 7.07 (m, 3H), 7.03 – 7.00 (m, 1H), 3.81 (s, 2H), 2.77 (t, J = 5.5 Hz, 2H), 2.61 (t, J = 5.5 Hz, 2H), 1.44 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.4, 136.2, 135.3, 128.7, 128.0, 126.8, 126.2, 126.0, 125.7, 125.3, 60.0, 48.6, 44.8, 30.4, 23.9 |
| HRMS (ESI) | m/z calcd for C₁₈H₂₂N [M + H]⁺ 252.1747; found 252.1747 |
| IR (ATR) νmax | 3084, 2973, 1600, 1492, 1372, 1236, 741, 700 cm⁻¹ |
| Identifier | 33 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.19 (d, J = 8.5 Hz, 2H), 6.84 (d, J = 8.5 Hz, 2H), 4.35 (s, 4H), 3.80 (s, 3H), 3.33 (q, J = 6.5 Hz, 1H), 2.42 – 2.15 (m, 4H), 1.88 – 1.75 (m, 4H), 1.33 (d, J = 6.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.4, 135.6, 128.6, 113.4, 82.0, 63.9, 55.2, 47.4, 38.7, 35.2, 19.3 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₄NO₂ [M + H]⁺ 262.1802; found 262.1802 |
| IR (ATR) νmax | 3061, 2925, 1610, 1510, 1372, 1243, 1177, 832, 741 cm⁻¹ |
| Identifier | 34 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.30 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 3.79 (q, J = 6.5 Hz, 1H), 2.72 – 2.62 (m, 4H), 1.65 – 1.55 (m, 8H), 1.40 (d, J = 6.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.4, 128.8, 113.4 (overlapped with 2C), 62.9, 55.2, 51.9, 28.2, 27.0, 18.0 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄NO [M + H]⁺ 234.1853; found 234.1852 |
| IR (ATR) νmax | 3061, 2965, 1610, 1509, 1366, 1241, 1175, 732, 698 cm⁻¹ |
| Identifier | 35 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.28 (d, J = 9.0 Hz, 2H), 6.85 (d, J = 9.0 Hz, 2H), 3.81 – 3.75 (m, 1H), 3.80 (s, 3H), 3.61 (d, J = 10.0 Hz, 1H), 3.57 (dd, J = 10.0, 2.0 Hz, 1H), 3.40 – 3.33 (m, 2H), 3.29 (q, J = 6.5 Hz, 1H), 2.80 (d, J = 5.0 Hz, 1H), 2.00 – 1.68 (m, 4H), 1.25 (d, J = 6.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.5, 137.5, 128.4, 113.6, 73.5, 73.3, 58.7, 58.2, 57.6, 55.2, 25.1, 24.7, 22.0 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₂NO₂ [M + H]⁺ 248.1645; found 248.1645 |
| IR (ATR) νmax | 3059, 2947, 1610, 1510, 1365, 1241, 1172, 831, 769 cm⁻¹ |
| Identifier | 36 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.52 (dd, J = 7.5, 1.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.25 (t, J = 7.5 Hz, 1H), 6.61 (d, J = 9.0 Hz, 2H), 6.30 (d, J = 9.0 Hz, 2H), 3.67 (s, 3H), 1.60 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 152.0, 147.8, 140.1, 128.4, 126.2, 125.7, 117.1, 114.3, 56.0, 55.6, 30.6 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₀NO [M + H]⁺ 242.1540; found 2442.1539 |
| IR (ATR) νmax | 3402, 3077, 2989, 1601, 1507, 1379, 1244, 1179, 777, 710 cm⁻¹ |
| Identifier | 37 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.51 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 6.82 (d, J = 8.0 Hz, 2H), 6.26 (d, J = 8.0 Hz, 2H), 3.90 (br s, 1H), 2.16 (s, 3H), 1.62 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.7, 143.7, 129.2, 128.5, 126.3, 126.2, 125.6, 115.5, 55.7, 30.7, 20.3 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1590 |
| IR (ATR) νmax | 3410, 3049, 2977, 1615, 1513, 1382, 1183, 760, 699 cm⁻¹ |
| Identifier | 38 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.51 (dd, J = 8.0, 1.5 Hz, 2H), 7.33 (dd, J = 8.0 Hz, 2H), 7.23 (t, J = 8.0 Hz, 1H), 7.00 (dd, J = 8.5, 7.5 Hz, 2H), 6.60 (t, J = 7.5 Hz, 1H), 6.33 (dd, J = 8.5, 1.5 Hz, 2H), 4.04 (br s, 1H), 1.64 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.4, 146.1, 128.7, 128.5, 126.3, 125.6, 117.0, 115.3, 55.7, 30.7 |
| HRMS (ESI) | m/z calcd for C₁₅H₁₈N [M + H]⁺ 212.1434; found 212.1434 |
| IR (ATR) νmax | 3419, 3082, 2978, 1599, 1490, 1378, 1176, 761, 701 cm⁻¹ |
| Identifier | 39 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.47 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 6.93 (d, J = 8.5 Hz, 2H), 6.24 (d, J = 8.5 Hz, 2H), 4.06 (br s, 1H), 1.62 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.9, 144.6, 128.6, 128.5, 126.5, 125.5, 121.7, 116.2, 55.9, 30.5 |
| HRMS (ESI) | m/z calcd for C₁₅H₁₇NCl [M + H]⁺ 246.1044; found 246.1042 |
| IR (ATR) νmax | 3414, 3085, 2978, 1595, 1490, 1380, 1178, 765, 695 cm⁻¹ |
| Identifier | 40 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.42 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.25 (t, J = 7.5 Hz, 1H), 7.23 (d, J = 8.5 Hz, 2H), 6.29 (d, J = 8.5 Hz, 2H), 4.66 (br s, 1H), 1.67 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.3, 145.7, 133.1, 128.8, 126.8, 125.2, 120.4, 114.5, 98.5, 56.1, 30.4 |
| HRMS (ESI) | m/z calcd for C₁₆H₁₇N₂ [M + H]⁺ 237.1386; found 237.1387 |
| IR (ATR) νmax | 3367, 3059, 2979, 2210, 1604, 1517, 1365, 1172, 766, 700 cm⁻¹ |
| Identifier | 41 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.59 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.53 (dd, J = 8.0, 8.0 Hz, 2H), 7.35 – 7.31 (m, 3H), 7.24 (dd, J = 8.0, 8.0 Hz, 2H), 7.11 (t, J = 8.0 Hz, 1H), 6.75 (dd, J = 8.5, 2.0 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 4.23 (br s, 1H), 1.70 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.0, 143.5, 134.6, 128.6, 128.4, 127.4, 127.1, 126.4, 126.0, 125.9, 125.6, 121.9, 119.2, 108.3, 56.0, 30.6 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₀N [M + H]⁺ 262.1590; found 262.1589 |
| IR (ATR) νmax | 3412, 3081, 2969, 1600, 1519, 1380, 1188, 748, 698 cm⁻¹ |
| Identifier | 42 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 8.04 (d, J = 4.0 Hz, 1H), 7.49 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.18 – 7.13 (m, 1H), 6.50 (dd, J = 7.0, 5.0 Hz, 1H), 5.82 (d, J = 7.5 Hz, 1H), 5.18 (br s, 1H), 1.68 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 157.4, 148.3, 146.7, 136.7, 128.6, 126.5, 125.4, 112.9, 108.0, 55.2, 30.4 |
| HRMS (ESI) | m/z calcd for C₁₄H₁₇N₂ [M + H]⁺ 213.1386; found 213.1386 |
| IR (ATR) νmax | 3278, 3081, 2975, 1600, 1576, 1442, 1382, 1193, 765, 701 cm⁻¹ |
| Identifier | 43 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.61 (d, J = 8.5 Hz, 2H), 7.34 (t, J = 8.0 Hz, 2H), 7.23 – 7.20 (m, 1H), 7.19 – 7.15 (m, 4H), 6.93 (t, J = 7.0 Hz, 2H), 6.79 (d, J = 8.0 Hz, 4H), 1.56 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.0, 146.7, 128.8, 128.6, 126.1, 125.2, 124.7, 121.6, 61.3, 30.0 |
| HRMS (ESI) | m/z calcd for C₂₁H₂₂N [M + H]⁺ 288.1747; found 288.1750 |
| IR (ATR) νmax | 3069, 2992, 1586, 1487, 1386, 1172, 751, 702 cm⁻¹ |
| Identifier | 44 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.53 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.19 (dd, J = 7.5, 7.5 Hz, 2H), 7.02 (d, J = 7.5 Hz, 2H), 6.96 (t, J = 7.5 Hz, 1H), 2.70 (s, 3H), 1.46 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 150.2, 148.9, 128.1, 127.9, 126.2, 126.1, 125.2, 122.1, 60.9, 36.8, 27.1 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1591 |
| IR (ATR) νmax | 3084, 2975, 1596, 1490, 1380, 1179, 752, 698 cm⁻¹ |
| Identifier | 45 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.56 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.03 (d, J = 7.5 Hz, 1H), 6.88 (dd, J = 7.5, 7.5 Hz, 1H), 6.53 (dd, J = 7.5, 7.5 Hz, 1H), 5.63 (d, J = 7.5 Hz, 1H), 3.58 (t, J = 7.5 Hz, 2H), 2.99 (t, J = 7.5 Hz, 2H), 1.52 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 150.0, 148.6, 131.3, 128.5 (overlapped with 2C), 126.3, 125.4, 124.0, 116.9, 111.2, 58.5, 48.8, 28.2, 25.6 |
| HRMS (ESI) | m/z calcd for C₁₇H₂₀N [M + H]⁺ 238.1590; found 238.1592 |
| IR (ATR) νmax | 3058, 2973, 1604, 1483, 1382, 1191, 744, 698 cm⁻¹ |
| Identifier | 46 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 8.09 (d, J = 7.5 Hz, 2H), 7.35 – 7.27 (m, 6H), 7.26 – 7.20 (m, 3H), 7.16 (dd, J = 7.5, 7.5 Hz, 2H), 2.24 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.6, 140.9, 128.8, 126.8, 125.1, 124.9, 124.4, 119.8, 118.7, 113.7, 64.1, 31.2 |
| HRMS (ESI) | m/z calcd for C₂₁H₂₀N [M + H]⁺ 286.1590; found 286.1590 |
| IR (ATR) νmax | 3059, 2980, 1592, 1493, 1387, 1179, 744, 696 cm⁻¹ |
| Identifier | 47 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.50 (d, J = 7.5 Hz, 2H), 7.34 (dd, J = 7.5, 7.5 Hz, 2H), 7.28 (t, J = 7.5 Hz, 1H), 6.99 – 6.93 (m, 4H), 6.81 (td, J = 7.0, 2.0 Hz, 2H), 6.68 – 6.64 (m, 2H), 1.56 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 154.4, 147.6, 135.0, 128.0, 127.0, 126.8, 126.3, 124.5, 122.6, 116.2, 65.3, 28.6 |
| HRMS (ESI) | m/z calcd for C₂₁H₂₀NO [M + H]⁺ 302.1540; found 302.1538 |
| IR (ATR) νmax | 3058, 2987, 1489, 1382, 1263, 1182, 758, 700 cm⁻¹ |
| Identifier | 48 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.62 (d, J = 7.5 Hz, 2H), 7.39 (dd, J = 7.5, 7.5 Hz, 2H), 7.27 (t, J = 7.5 Hz, 1H), 7.23 – 7.20 (m, 2H), 7.03 – 6.97 (m, 4H), 6.97 – 6.92 (m, 2H), 1.75 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.7, 145.5, 132.9, 128.2, 127.5, 126.9, 126.4, 126.0, 124.6, 123.5, 64.9, 32.3 |
| HRMS (ESI) | m/z calcd for C₂₁H₂₀NS [M + H]⁺ 318.1311; found 318.1312 |
| IR (ATR) νmax | 3057, 2979, 1589, 1492, 1389, 1174, 751, 705 cm⁻¹ |
| Identifier | 49 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.63 (s, 1H), 7.31 (dd, J = 7.0, 7.0 Hz, 2H), 7.27 (t, J = 7.0, 1H), 7.09 (s, 1H), 7.06 (d, J = 7.0 Hz, 2H), 6.91 (s, 1H), 1.92 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.0, 135.6, 129.2, 128.6, 127.5, 124.8, 117.8, 60.0, 30.4 |
| HRMS (ESI) | m/z calcd for C₁₂H₁₅N₂ [M + H]⁺ 187.1230; found 187.1229 |
| IR (ATR) νmax | 3123, 3088, 2984, 1491, 1373, 1230, 1189, 770, 701, 663 cm⁻¹ |
| Identifier | 50 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.58 (d, J = 2.0 Hz, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.03 – 7.00 (m, 2H), 6.29 (dd, J = 2.0, 2.0 Hz, 1H), 1.98 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.8, 138.8, 128.4, 127.6, 127.1, 124.9, 105.2, 63.5, 29.8 |
| HRMS (ESI) | m/z calcd for C₁₂H₁₅N₂ [M + H]⁺ 187.1230; found 187.1230 |
| IR (ATR) νmax | 3141, 3088, 2983, 1601, 1496, 1388, 1246, 747, 697, 625 cm⁻¹ |
| Identifier | 51 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.94 (s, 1H), 7.76 (d, J = 9.0 Hz, 1H), 7.64 (d, J = 9.0 Hz, 1H), 7.32 – 7.23 (m, 4H), 7.10 – 7.04 (m, 3H), 2.13 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.2, 146.0, 128.5 (overlapped with 2C), 127.4, 125.7, 125.1, 121.5, 121.5, 120.2, 117.8, 65.3, 30.1 |
| HRMS (ESI) | m/z calcd for C₁₆H₁₇N₂ [M + H]⁺ 237.1386; found 237.1387 |
| IR (ATR) νmax | 3131, 3053, 2981, 1626, 1497, 1378, 1187, 760, 698 cm⁻¹ |
| Identifier | 52 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.72 (d, J = 1.0 Hz, 1H), 7.43 (d, J = 1.0 Hz, 1H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.29 (t, J = 7.5 Hz, 1H), 7.11 (d, J = 7.5 Hz, 2H), 2.01 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 144.8, 133.7, 128.7, 127.8, 124.9, 122.3, 64.1, 29.8 |
| HRMS (ESI) | m/z calcd for C₁₁H₁₄N₃ [M + H]⁺ 188.1182; found 188.1181 |
| IR (ATR) νmax | 3150, 3061, 2939, 1601, 1497, 1371, 1206, 762, 698 cm⁻¹ |
| Identifier | 53 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.36 (d, J = 8.0 Hz, 1H), 7.34 – 7.32 (m, 2H), 7.29 (dd, J = 8.0, 8.0 Hz, 2H), 7.25 – 7.19 (m, 3H), 7.16 (d, J = 6.5 Hz, 1H), 3.69 (q, J = 7.5 Hz, 1H), 3.63 (s, 3H), 1.85 (s, 3H), 1.78 (br s, 2H), 1.47 (d, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 175.0 (overlapped with 2C), 149.9, 149.4, 140.3 (overlapped with 2C), 128.3 (overlapped with 2C), 128.1(overlapped with 2C), 126.4 (overlapped with 2C), 126.1 (overlapped with 2C), 125.4 (overlapped with 2C), 125.4 (overlapped with 2C), 125.3 (overlapped with 2C), 125.2 (overlapped with 2C), 58.5 (overlapped with 2C), 51.9 (overlapped with 2C), 45.5 (overlapped with 2C), 31.7 (overlapped with 2C), 18.7, 18.6 |
| HRMS (ESI) | m/z calcd for C₁₈H₂₂NO₂ [M + H]⁺ 284.1645; found 284.1643 |
| IR (ATR) νmax | 3373, 3084, 2934, 1731, 1599, 1487, 1373, 1163, 767, 700 cm⁻¹ |
| NMR reporting qualifier | mixture of diastereoisomers |
| Identifier | 54 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.33 (d, J = 9.0 Hz, 2H), 6.86 (d, J = 9.0, 2H), 3.80 (s, 3H), 3.04 (s, 2H), 1.44 (s, 6H), 1.82 (br s, 1H), 1.42 (s, 9H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 172.1, 158.0, 139.0, 126.9, 113.5, 81.0, 55.2, 55.1, 46.1, 29.4, 28.0 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄NO₂ [M + H]⁺ 280.1907; found 280.1908 |
| IR (ATR) νmax | 3334, 3057, 2974, 1730, 1610, 1511, 1380, 1239, 1152, 736 cm⁻¹ |
| Identifier | 55 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.57 (d, J = 7.5 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 7.34 (t, J = 7.5 Hz, 1H), 7.28 (d, J = 8.5 Hz, 2H), 7.27 – 7.20 (m, 3H), 7.09 (dd, J = 7.5, 1.5 Hz, 2H), 3.51 (s, 3H), 3.25 (dd, J = 8.0, 6.0 Hz, 1H), 2.83 (dd, J = 13.0, 6.0 Hz, 1H), 2.76 (dd, J = 13.0, 8.0 Hz, 1H), 2.02 (br s, 1H), 1.40 (s, 3H), 1.35 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 176.9, 146.1, 140.9, 139.0, 137.4, 129.5, 128.7, 128.2, 127.1, 126.9, 126.6, 126.5, 126.5, 58.1, 56.1, 51.6, 41.5, 31.3, 27.7 |
| HRMS (ESI) | m/z calcd for C₂₅H₂₈NO₂ [M + H]⁺ 374.2115; found 374.2116 |
| IR (ATR) νmax | 3350, 3085, 2964, 1723, 1486, 1379, 1163, 763, 691 cm⁻¹ |
| Identifier | 56 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 (d, J = 7.5 Hz, 2H), 7.31 (d, J = 7.5 Hz, 2H), 7.29 – 7.24 (m, 4H), 7.22 – 7.17 (m, 2H), 3.68 (s, 3H), 3.60 (dd, J = 6.5, 6.0 Hz, 1H), 3.46 (s, 3H), 2.76 (br s, 1H), 2.63 (dd, J = 15.0, 6.5 Hz, 1H), 2.54 (dd, J = 15.0, 6.0 Hz, 1H), 1.75 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 174.8, 171.2, 148.0, 147.1, 127.9, 127.9, 127.2, 127.2, 126.6, 126.5, 62.7, 52.9, 52.0, 51.7, 40.3, 27.9 |
| HRMS (ESI) | m/z calcd for C₂₀H₂₄NO₄ [M + H]⁺ 342.1700; found 342.1700 |
| IR (ATR) νmax | 3334, 3085, 2980, 1735, 1598, 1492, 1372, 1166, 761, 699 cm⁻¹ |
| Identifier | 57 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.46 (d, J = 7.5 Hz, 2H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 3.52 (s, 3H), 2.76 (d, J = 6.0 Hz, 1H), 1.74 – 1.67 (m, 1H), 1.42 (s, 3H), 1.41 (s, 3H), 0.88 (d, J = 7.0 Hz, 3H), 0.81 (d, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 177.3, 147.3, 127.8, 126.4, 126.4, 61.4, 55.7, 51.3, 32.9, 30.2, 28.4, 19.0, 18.8 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄NO₂ [M + H]⁺ 250.1802; found 250.1802 |
| IR (ATR) νmax | 3332, 3088, 2963, 1732, 1495, 1382, 1169, 764, 699 cm⁻¹ |
| Identifier | 58 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.59 (d, J = 7.5 Hz, 2H), 7.54 (d, J = 9.0 Hz, 2H), 7.51 (d, J = 9.0 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.43 (t, J = 7.5, 1H), 3.56 (s, 3H), 3.18 (dd, J = 8.0, 5.5 Hz, 1H), 2.56 (ddd, J = 13.0, 8.5, 5.5 Hz, 1H), 2.49 (ddd, J = 13.0, 8.5, 5.5 Hz, 1H), 2.11 (br s, 1H), 2.03 (s, 3H), 1.80 – 1.67 (m, 2H), 1.46 (s, 3H), 1.45 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 177.2, 146.2, 140.8, 139.3, 128.7, 127.1, 127.0, 126.7, 126.6, 55.8, 54.9, 51.8, 34.7, 30.5, 30.3, 28.3, 15.2 |
| HRMS (ESI) | m/z calcd for C₂₁H₂₈NO₂S [M + H]⁺ 358.1835; found 358.1837 |
| IR (ATR) νmax | 3328, 3078, 2915, 1732, 1600, 1486, 1371, 1167, 766, 697 cm⁻¹ |
| Identifier | 59 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.58 (d, J = 7.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.34 (t, J = 7.5, 1H), 3.61 (s, 3H), 3.55 (dd, J = 10.0, 5.0 Hz, 1H), 3.47 (dd, J = 10.0, 6.0 Hz, 1H), 3.26 (dd, J = 6.0, 5.0 Hz, 1H), 2.83 (br s, 1H), 1.52 (br s, 1H), 1.51 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 174.8, 145.7, 140.6, 139.6, 128.7, 127.2, 127.0, 126.9, 126.5, 63.8, 57.4, 55.9, 52.2, 29.8, 29.2 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₄NO₃ [M + H]⁺ 314.1751; found 314.1756 |
| IR (ATR) νmax | 3442, 3334, 3056, 2968, 1732, 1487, 1383, 1171, 766, 697 cm⁻¹ |
| Identifier | 60 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 8.13 (d, J = 8.5 Hz, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.46 – 7.40 (m, 4H), 7.36 – 7.29 (m, 3H), 7.26 (t, J = 7.0 Hz, 1H), 7.17 (d, J = 7.0 Hz, 2H), 4.85 (ddd, J = 8.5, 5.5, 5.5 Hz, 1H), 3.70 (s, 3H), 3.58 (s, 3H), 3.27 (dd, J = 6.0, 5.0 Hz, 1H), 3.15 (dd, J = 13.5, 5.5 Hz, 1H), 3.08 (dd, J = 13.5, 5.5 Hz, 1H), 2.65 (dd, J = 13.5, 6.0 Hz, 1H), 2.37 (dd, J = 13.5, 6.0 Hz, 1H), 2.29 (br s, 1H), 1.46 (s, 3H), 1.43 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 173.6, 171.9, 171.8, 145.9, 140.6, 139.6, 136.0, 129.4, 128.7, 128.5, 127.2, 127.1, 127.0, 126.9, 126.3, 56.0, 53.7, 52.6, 52.1, 51.7, 38.2, 37.6, 30.3, 27.5 |
| HRMS (ESI) | m/z calcd for C₃₀H₃₅N₂O₅ [M + H]⁺ 503.2541; found 503.2541 |
| IR (ATR) νmax | 3334, 3060, 2952, 1735, 1487, 1360, 1174, 767, 698 cm⁻¹ |
| Identifier | 61 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.32 – 7.26 (m, 4H), 7.22 – 7.18 (m, 1H), 6.71 (d, J = 7.5 Hz, 1H), 6.62 – 6.58 (m, 2H), 5.92 (s, 2H), 2.65 (t, J = 7.0 Hz, 2H), 2.64 (t, J = 7.0 Hz, 2H), 1.55 (br s, 1H), 1.43 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.5, 145.8, 133.8, 128.1, 126.1, 125.6 (overlapped with 2C), 121.6, 109.1, 108.1, 100.8, 55.7, 44.4, 36.6, 29.5 |
| HRMS (ESI) | m/z calcd for C₁₈H₂₂NO₂ [M + H]⁺ 284.1645; found 284.1644 |
| IR (ATR) νmax | 3327, 3084, 2967, 1602, 1487, 1379, 1243, 1184, 763, 699 cm⁻¹ |
| Identifier | 62 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.30 (d, J = 8.5 Hz, 2H), 7.26 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 7.15 (d, J = 7.5 Hz, 2H), 6.83 (d, J = 8.5 Hz, 2H), 4.01 (q, J = 6.5 Hz, 1H), 3.79 (s, 3H), 2.73 (d, J = 13.0 Hz, 1H), 2.60 (d, J = 13.0 Hz, 1H), 1.28 (d, J = 6.5 Hz, 3H), 0.94 (s, 3H), 0.90 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.0, 141.4, 138.7, 130.6, 127.8, 127.3, 126.0, 113.5, 55.2, 54.3, 51.5, 48.5, 28.0, 27.6, 27.5 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₆NO [M + H]⁺ 284.2009; found 284.2008 |
| IR (ATR) νmax | 3340, 3083, 2961, 1610, 1509, 1364, 1239, 1169, 701 cm⁻¹ |
| Identifier | 63 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.50 (d, J = 7.5 Hz, 2H), 7.26 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 1.94 – 1.88 (m, 1H), 1.59 (br s, 1H), 1.52 (s, 6H), 1.27 (s, 2H), 1.21 (d, J = 12.0 Hz, 2H), 1.13 (s, 4H), 1.10 (d, J = 12.0 Hz, 2H), 0.99 (d, J = 12.0 Hz, 1H), 0.95 (d, J = 12.0 Hz, 1H), 0.70 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 151.3, 127.6, 125.8, 55.5, 54.3, 52.2, 50.6, 43.5, 42.7, 33.3, 32.4, 30.5, 30.4 |
| HRMS (ESI) | m/z calcd for C₂₁H₃₂N [M + H]⁺ 298.2530; found 298.2528 |
| IR (ATR) νmax | 3354, 3084, 2994, 1601, 1494, 1376, 1193, 763, 699 cm⁻¹ |
| Identifier | 64 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.61 (d, J = 7.5 Hz, 2H), 7.55 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.33 (t, J = 7.5 Hz, 1H), 7.19 (d, J = 8.0 Hz, 1H), 6.99 (d, J = 8.0 Hz, 1H), 6.91 (s, 1H), 2.92 – 2.78 (m, 3H), 2.30 – 2.23 (m, 2H), 2.00 (d, J = 12.0 Hz, 1H), 1.81 – 1.69 (m, 2H), 1.67 – 1.48 (m, 5H), 1.44 (s, 6H), 1.42– 1.37 (m, 1H), 1.32– 1.27 (m, 1H), 1.24 (d, J = 7.0 Hz, 6H), 1.19 (s, 3H), 0.84 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.7, 147.6, 145.4, 141.0, 138.8, 134.9, 128.7, 127.0 (overlapped with 2C), 126.8, 126.6, 126.5, 124.3, 123.8, 55.1, 53.9, 44.4, 38.5, 37.4, 36.7, 36.0, 33.4, 30.3, 30.0, 29.5, 25.5, 24.0, 19.8, 18.9, 18.7 |
| HRMS (ESI) | m/z calcd for C₃₅H₄₆N [M + H]⁺ 480.3625; found 480.3625 |
| IR (ATR) νmax | 3342, 3054, 2958, 1601, 1496, 1380, 1178, 764, 696 cm⁻¹ |
| Identifier | 65 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.65 (d, J = 8.0 Hz, 2H), 7.45 (dd, J = 8.0, 1.5 Hz, 2H), 7.32 (dd, J = 8.0, 8.0 Hz, 2H), 7.23 (t, J = 8.0 Hz, 1H), 6.29 (d, J = 9.0 Hz, 2H), 4.55 (br s, 1H), 4.26 (q, J = 7.0 Hz, 2H), 1.67 (s, 6H), 1.20 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 166.8, 149.9, 146.3, 130.8, 128.7, 126.6, 125.3, 118.4, 113.8, 60.0, 56.0, 30.6, 14.4 |
| HRMS (ESI) | m/z calcd for C₁₈H₂₂NO₂ [M + H]⁺ 284.1645; found 284.1644 |
| IR (ATR) νmax | 3370, 3085, 2983, 1683, 1603, 1366, 1267, 1171, 767, 699 cm⁻¹ |
| Identifier | 66 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.52 (d, J = 7.5 Hz, 2H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 3.58 (dd, J = 8.5, 3.0 Hz, 1H), 3.56 (s, 3H), 2.94 (ddd, J = 8.5, 6.5, 3.0 Hz, 1H), 2.62 (ddd, J = 8.5, 8.5, 6.5 Hz, 1H), 1.99 – 1.87 (m, 2H), 1.87 – 1.78 (m, 1H), 1.74 – 1.65 (m, 1H), 1.43 (s, 3H), 1.37 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 177.5, 148.0, 127.8, 126.5, 126.3, 59.7, 58.8, 51.5, 48.1, 31.8, 25.7, 24.8, 23.8 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₂NO₂ [M + H]⁺ 248.1645; found 248.1645 |
| IR (ATR) νmax | 3085, 2970, 1729, 1600, 1492, 1383, 1156, 765, 700 cm⁻¹ |
| Identifier | 67 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.13 – 7.08 (m, 4H), 7.07 – 7.02 (m, 4H), 6.89 (ddd, J = 7.5, 7.5, 1.0 Hz, 2H), 6.77 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 3.70 (t, J = 7.0 Hz, 2H), 3.43 (q, J = 7.0 Hz, 1H), 3.05 (s, 4H), 2.45 (ddd, J = 12.0, 7.5, 7.5 Hz, 1H), 2.23 (ddd, J = 12.0, 7.5, 7.5 Hz, 1H), 2.09 (s, 3H), 1.72 – 1.64 (m, 2H), 1.25 (d, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.3, 148.3, 136.1, 134.2, 129.7, 128.5, 126.2, 122.2, 119.9, 113.4, 62.7, 55.2, 51.9, 48.5, 38.4, 32.2, 25.6, 18.4 |
| HRMS (ESI) | m/z calcd for C₂₇H₃₃N₂O [M + H]⁺ 401.2588; found 401.2588 |
| IR (ATR) νmax | 3060, 2964, 1609, 1463, 1368, 1243, 1174, 832, 751 cm⁻¹ |
| Identifier | 68 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.31 (d, J = 9.0 Hz, 2H), 7.25 (d, J = 7.5 Hz, 2H), 7.22 – 7.18 (m, 2H), 7.12 – 7.03 (m, 4H), 6.89 (d, J = 9.0 Hz, 2H), 4.26 (s, 1H), 3.82 (s, 3H), 3.65 (q, J = 7.0 Hz, 1H), 2.67 (ddd, J = 12.5, 7.5, 7.5 Hz, 1H), 2.54 (ddd, J = 12.5, 7.5, 7.5 Hz, 1H), 2.43 – 2.31 (m, 2H), 2.30 (s, 3H), 1.95 – 1.84 (m, 2H), 1.84 – 1.77 (m, 2H), 1.57 – 1.51 (m, 2H), 1.42 (d, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.4, 145.6, 145.0, 136.1, 128.8, 125.2, 125.1, 123.2, 121.4, 113.4, 62.7, 55.2, 55.2, 44.8, 44.5, 38.7, 29.6, 28.7, 27.7, 22.6, 18.6 |
| HRMS (ESI) | m/z calcd for C₂₉H₃₄NO [M + H]⁺ 412.2635; found 412.2635 |
| IR (ATR) νmax | 3066, 2974, 1609, 1509, 1463, 1369, 1238, 1176, 831, 756 cm⁻¹ |
| Identifier | 69 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (d, J = 8.5 Hz, 2H), 7.29 – 7.24 (m, 4H), 7.22 – 7.18 (m, 1H), 7.16 (dd, J = 7.5, 7.5 Hz, 2H), 7.11 (t, J = 7.5 Hz, 1H), 7.05 (d, J = 7.5 Hz, 1H), 6.93 (t, J = 7.5 Hz, 1H), 6.73 (t, J = 7.5 Hz, 1H), 6.55 (d, J = 7.5 Hz, 1H), 5.18 (dd, J = 9.0, 3.5 Hz, 1H), 2.56 (ddd, J = 14.0, 8.0, 8.0 Hz, 1H), 2.43 (ddd, J = 12.5, 7.5, 4.0 Hz, 1H), 2.20 (s, 3H), 2.11 (s, 3H), 2.10 – 2.02 (m, 1H), 1.98 – 1.89 (m, 1H), 1.30 (s, 3H), 1.27 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 156.1, 149.7, 142.8, 130.4, 128.4, 127.8, 127.1, 127.0, 126.4, 126.0, 125.6, 119.8, 112.5, 77.1, 60.4, 47.6, 38.5, 35.0, 24.0, 23.9, 16.4 |
| HRMS (ESI) | m/z calcd for C₂₆H₃₂NO [M + H]⁺ 374.2479; found 374.2476 |
| IR (ATR) νmax | 3084, 2971, 1601, 1490, 1376, 1238, 1175, 764, 698 cm⁻¹ |
| Identifier | 70 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.59 (d, J = 8.0 Hz, 2H), 7.36 (d, J = 7.5 Hz, 1H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 7.13 (s, 1H), 7.09 – 7.03 (m, 2H), 7.00 (d, J = 7.5 Hz, 1H), 6.85 – 6.80 (m, 1H), 6.49 (d, J = 8.0 Hz, 1H), 3.15 – 2.98 (m, 4H), 2.72 – 2.63 (m, 4H), 2.35 (s, 3H), 2.30 (s, 3H), 1.40 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.5, 149.3, 142.4, 139.1, 136.2, 134.4, 131.6, 128.1, 127.9, 127.7, 126.2, 126.1, 126.1, 125.4, 124.0, 119.7, 59.6, 52.5, 46.5, 24.2, 21.2, 20.6 |
| HRMS (ESI) | m/z calcd for C₂₇H₃₃N₂S [M + H]⁺ 417.2359; found 417.2360 |
| IR (ATR) νmax | 3081, 2974, 1601, 1469, 1373, 1240, 1187, 753, 701 cm⁻¹ |
| Identifier | 71 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.57 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 7.17 (dd, J = 8.5, 5.5 Hz, 2H), 6.96 (dd, J = 8.5, 8.5 Hz, 2H), 6.60 (d, J = 8.5 Hz, 1H), 6.27 (d, J = 2.5 Hz, 1H), 6.07 (dd, J = 8.5, 2.5 Hz, 1H), 5.87 (s, 2H), 3.53 (dd, J = 9.5, 2.5 Hz, 1H), 3.41 (dd, J = 9.5, 6.5 Hz, 1H), 3.24 – 3.18 (m, 1H), 2.92 – 2.86 (m, 1H), 2.46 – 2.37 (m, 1H), 2.23 – 2.08 (m, 3H), 1.79 – 1.72 (m, 2H), 1.393 (s, 3H), 1.386 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 161.4 (d, JC-F = 242.5 Hz), 154.4, 149.5, 148.0, 141.4, 140.2, 128.8 (d, JC-F = 7.5 Hz), 128.0, 126.1, 125.9, 115.2 (d, JC-F = 17.5 Hz), 107.8, 105.7, 101.0, 98.1, 69.9, 60.0, 50.5, 47.1, 44.7, 42.9, 35.3, 24.9, 23.7 |
| ¹⁹F NMR (376 MHz, CDCl₃) | δ −116.93 |
| HRMS (ESI) | m/z calcd for C₂₈H₃₁NO₃F [M + H]⁺ 448.2281; found 448.2280 |
| IR (ATR) νmax | 3084, 2972, 1604, 1487, 1373, 1241, 1178, 766, 700 cm⁻¹ |
| Identifier | 72 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.33 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 2.30 (t, J = 7.5 Hz, 2H), 1.43 (s, 6H), 1.42 – 1.35 (m, 2H), 1.32 – 1.25 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 157.8, 140.1, 126.8, 113.3, 55.2, 55.2, 42.7, 33.1, 29.7, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₄NO [M + H]⁺ 222.1853; found 222.1853 |
| IR (ATR) νmax | 3324, 3039, 2926, 1589, 1488, 1231, 1168, 752, 691 cm⁻¹ |
| Identifier | 73 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.35 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 2.48 (s, 3H), 2.30 (t, J = 7.0 Hz, 2H), 1.56 (br s, 1H), 1.44 (s, 6H), 1.42 – 1.35 (m, 2H), 1.32 – 1.24 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 145.0, 135.7, 126.5, 126.3, 55.5, 42.7, 33.0, 29.5, 20.5, 16.0, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₄NS [M + H]⁺ 238.1624; found 238.1622 |
| IR (ATR) νmax | 3316, 3076, 2957, 1596, 1491, 1378, 1182, 751, 698 cm⁻¹ |
| Identifier | 74 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.35 – 7.30 (m, 4H), 2.32 (t, J = 7.5 Hz, 2H), 1.45 (s, 6H), 1.44 – 1.37 (m, 2H), 1.32 (s, 9H), 1.31 – 1.25 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.7, 144.8, 125.3, 124.9, 55.4, 42.7, 34.3, 33.1, 31.4, 29.6, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₇H₃₀N [M + H]⁺ 248.2373; found 248.2372 |
| IR (ATR) νmax | 3315, 3088, 2956, 1510, 1464, 1182, 828, 696 cm⁻¹ |
| Identifier | 75 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.60 (d J = 7.5 Hz, 2H), 7.56 (d, J = 8.0 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.33 (t, J = 7.5 Hz, 1H), 2.35 (t, J = 7.0 Hz, 2H), 1.49 (s, 6H), 1.46 – 1.39 (m, 2H), 1.35 – 1.27 (m, 2H), 0.87 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.2, 140.9, 138.8, 128.7, 127.0, 126.9, 126.8, 126.1, 55.5, 42.7, 33.1, 29.6, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₆N [M + H]⁺ 268.2060; found 268.2063 |
| IR (ATR) νmax | 3327, 3078, 2957, 1601, 1486, 1378, 1181, 764, 733, 695 cm⁻¹ |
| Identifier | 76 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.39 (dd, J = 8.5, 3.0 Hz, 2H), 6.99 (dd, J = 8.5, 8.5 Hz, 2H), 2.29 (t, J = 7.5 Hz, 2H), 1.43 (s, 6H), 1.42 – 1.36 (m, 2H), 1.32 – 1.25 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 160.3 (d, JC-F = 257.5 Hz), 143.8, 127.3 (d, JC-F = 7.5 Hz), 114.6 (d, JC-F = 21.3 Hz), 55.4, 42.6, 33.1, 29.8, 20.5, 14.0 |
| ¹⁹F NMR (125 MHz, CDCl₃) | δ −117.73 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₁NF [M + H]⁺ 210.1653; found 210.1653 |
| IR (ATR) νmax | 3333, 3058, 2959, 1601, 1507, 1379, 1222, 1182, 833, 697 cm⁻¹ |
| Identifier | 77 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.78 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 2.29 (t, J = 7.5 Hz, 2H), 1.47 (s, 6H), 1.44 – 1.38 (m, 2H), 1.34 (s, 12H), 1.30 – 1.26 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 134.7 (overlapped with 2C), 125.1, 83.7, 56.0, 42.8, 33.0, 29.5, 24.8, 20.5, 14.0 |
| IR (ATR) νmax | 3333, 3081, 2976, 1611, 1398, 1361, 1181, 1145, 660 cm⁻¹ |
| HRMS (ESI) | m/z calcd for C₁₉H₃₃BNO₂ [M + H]⁺ 318.2599; found 318.2599 |
| ¹³C NMR reporting qualifier | The boron-bound carbon was not detected |
| Identifier | 78 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.28 (d, J = 9.0 Hz, 2H), 6.72 (d, J = 9.0 Hz, 2H), 2.93 (s, 6H), 2.31 (t, J = 7.5 Hz, 2H), 1.43 (s, 6H), 1.42 – 1.36 (m, 2H), 1.32 – 1.24 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.9, 135.6, 126.3, 112.3, 55.1, 42.7, 40.7, 33.0, 29.5, 20.6, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₇N₂ [M + H]⁺ 235.2169; found 235.2170 |
| IR (ATR) νmax | 3322, 3073, 2928, 1613, 1520, 1373, 1238, 1166, 818, 730 cm⁻¹ |
| Identifier | 79 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.23 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 3.71 (q, J = 6.5 Hz, 1H), 2.48 (ddd, J = 14.0, 8.0, 5.0 Hz, 1H), 2.41 (ddd, J = 14.0, 8.0, 5.0 Hz, 1H), 1.49 – 1.38 (m, 2H), 1.33 (d, J = 6.5 Hz, 3H), 1.33 – 1.24 (m, 2H), 0.87 (t, J = 7.5, Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.4, 138.0, 127.5, 113.7, 57.7, 55.2, 47.5, 32.4, 24.3, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₂NO [M + H]⁺ 208.1696; found 208.1695 |
| IR (ATR) νmax | 3328, 3062, 2928, 1611, 1510, 1463, 1368, 1242, 1178, 830, 752 cm⁻¹ |
| Identifier | 80 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 6.97 (d, J = 1.5 Hz, 1H), 6.86 (dd, J = 8.0, 1.5 Hz, 1H), 6.75 (d, J = 8.0 Hz, 1H), 5.94 (s, 2H), 2.31 (t, J = 7.5 Hz, 2H), 1.54 (br s, 1H), 1.42 (s, 6H), 1.41 – 1.37 (m, 2H), 1.33 – 1.27 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.6, 145.6, 142.4, 118.6, 107.6, 106.6, 100.8, 55.6, 42.6, 33.1, 29.8, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₂NO₂ [M + H]⁺ 236.1645; found 236.1645 |
| IR (ATR) νmax | 3326, 3073, 2958, 1610, 1487, 1374, 1236, 1181, 1039, 808 cm⁻¹ |
| Identifier | 81 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 6.59 (s, 2H), 6.33 (s, 1H), 3.80 (s, 6H), 2.32 (t, J = 7.0 Hz, 2H), 1.42 (s, 6H), 1.40 – 1.37 (m, 2H), 1.34 – 1.26 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 160.6, 150.9, 104.2, 97.5, 55.9, 55.2, 42.7, 33.1, 29.6, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₆NO₂ [M + H]⁺ 252.1958; found 252.1959 |
| IR (ATR) νmax | 3326, 3088, 2956, 1593, 1454, 1378, 1202, 1150, 845 cm⁻¹ |
| Identifier | 82 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 6.80 (s, 2H), 4.29 (q, J = 7.0 Hz, 1H), 2.47 (ddd, J = 14.0, 8.0, 6.0 Hz, 1H), 2.45 – 2.33 (m, 1H), 2.40 (s, 6H), 2.24 (s, 3H), 1.48 – 1.41 (m, 2H), 1.38 (d, J = 7.0 Hz, 3H), 1.35 – 1.24 (m, 2H), 0.87 (t, J = 7.0, Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 137.5, 136.2, 135.5, 130.1, 54.0, 47.8, 32.7, 20.9, 20.7, 20.6, 20.4, 14.1 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₆N [M + H]⁺ 220.2060; found 220.2059 |
| IR (ATR) νmax | 3301, 3005, 2957, 1611, 1464, 1376, 1142, 850, 732 cm⁻¹ |
| Identifier | 83 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.83 – 7.80 (m, 4H), 7.61 (dd, J = 8.5, 1.5 Hz, 1H), 7.45 (dd, J = 8.5, 8.5 Hz, 2H), 2.32 (t, J = 7.0 Hz, 2H), 1.55 (s, 6H), 1.44 – 1.38 (m, 2H), 1.31 – 1.24 (m, 2H), 0.84 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 145.5, 133.2, 132.1, 128.0, 127.8, 127.4, 125.8, 125.5, 124.5, 124.1, 55.8, 42.8, 33.1, 29.5, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₇H₂₄N [M + H]⁺ 242.1903; found 242.1901 |
| IR (ATR) νmax | 3329, 3050, 2957, 1599, 1462, 1377, 1239, 1180, 855, 745, 699 cm⁻¹ |
| Identifier | 84 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.50 (d, J = 8.5 Hz, 1H), 7.43 (d, J = 8.5 Hz, 1H), 7.23 (ddd, J = 7.5, 7.5, 1.5 Hz, 1H), 7.19 (ddd, J = 7.5, 7.5, 1.5 Hz, 1H), 6.47 (s, 1H), 2.34 (t, J = 7.5 Hz, 2H), 1.57 (br s, 1H), 1.51 (s, 6H), 1.43 – 1.37 (m, 2H), 1.30 – 1.23 (m, 2H), 0.83 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 163.5, 154.6, 128.5, 123.5, 122.4, 120.5, 111.0, 101.9, 53.5, 43.2, 32.7, 26.9, 20.4, 13.9 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₂NO [M + H]⁺ 232.1697; found 232.1695 |
| IR (ATR) νmax | 3314, 3060, 2959, 1599, 1476, 1372, 1166, 1045, 751 cm⁻¹ |
| Identifier | 85 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.17 (d, J = 4.5 Hz, 1H), 6.92 (dd, J = 4.5, 4.5 Hz, 1H), 6.88 – 6.84 (m, 1H), 2.43 (t, J = 7.0 Hz, 2H), 1.53 (s, 6H), 1.45 – 1.39 (m, 2H), 1.34 – 1.26 (m, 2H), 0.87 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 154.8, 126.3, 123.5, 122.8, 55.1, 42.8, 32.8, 30.3, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₁H₂₀NS [M + H]⁺ 198.1311; found 198.1310 |
| IR (ATR) νmax | 3313, 3103, 3070, 2958, 1462, 1378, 1240, 1182, 844, 691 cm⁻¹ |
| Identifier | 86 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 8.18 (d, J = 2.0 Hz, 1H), 7.68 (d, J = 8.5 Hz, 1H), 6.71 (d, J = 8.5 Hz, 1H), 3.93 (s, 3H), 3.60 (dd, J = 6.5, 6.0 Hz, 1H), 2.31 (t, J = 7.0 Hz, 2H), 1.44 (s, 6H), 1.42 – 1.34 (m, 2H), 1.33 – 1.24 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 162.7, 144.1, 136.9, 135.8, 110.2, 54.2, 53.3, 42.6, 33.0, 29.4, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₃H₂₃N₂O [M + H]⁺ 223.1805; found 223.1805 |
| IR (ATR) νmax | 3314, 3088, 2958, 1603, 1491, 1372, 1284, 1247, 1181, 830 cm⁻¹ |
| Identifier | 87 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 (d, J = 7.5 Hz, 4H), 7.28 (dd, J = 7.5, 7.5 Hz, 4H), 7.19 (t, J = 7.5, 7.5 Hz, 2H), 2.35 (t, J = 7.0 Hz, 2H), 1.79 (s, 3H), 1.50 (br s, 1H), 1.47 – 1.41 (m, 2H), 1.35 – 1.28 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 148.4, 127.9, 127.0, 126.2, 62.4, 42.7, 33.0, 27.6, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₈H₂₄N [M + H]⁺ 254.1903; found 254.1902 |
| IR (ATR) νmax | 3333, 3084, 2956, 1599, 1491, 1370, 1182, 759, 698 cm⁻¹ |
| Identifier | 88 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.95 (d, J = 8.5 Hz, 2H), 7.44 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 6.82 (d, J = 8.5 Hz, 2H), 3.89 (s, 3H), 3.79 (s, 3H), 2.38 – 2.27 (m, 2H), 1.77 (s, 3H), 1.46 – 1.41 (m, 2H), 1.35 – 1.26 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 167.0, 158.0, 154.1, 139.7, 129.3, 128.0, 128.0, 127.0, 113.3, 62.1, 55.2, 52.0, 42.7, 33.0, 27.6, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₂₁H₂₈NO₂ [M + H]⁺ 342.2064; found 342.2063 |
| IR (ATR) νmax | 3332, 3092, 2954, 1721, 1608, 1509, 1276, 1247, 1179, 830 cm⁻¹ |
| Identifier | 89 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.46 (d, J = 7.5, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (t, J = 7.5, Hz, 1H), 7.19 (dd, J = 5.5, 1.0 Hz, 1H), 6.91 (dd, J = 5.5, 3.5 Hz, 1H), 6.80 – 6.76 (m, 1H), 2.45 (m, 2H), 1.86 (s, 3H), 1.57 (br s, 1H), 1.51 – 1.41 (m, 2H), 1.38 – 1.29 (m, 2H), 0.87 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 154.7, 147.6, 128.0, 126.7, 126.5, 126.2, 124.4, 124.0, 61.3, 42.9, 32.9, 29.0, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₂NS [M + H]⁺ 260.1468; found 260.1467 |
| IR (ATR) νmax | 3329, 3084, 2926, 1600, 1464, 1236, 1180, 764, 696 cm⁻¹ |
| Identifier | 90 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.69 (d, J = 7.5 Hz, 2H), 7.19 (dd, J = 7.5, 7.5 Hz, 2H), 7.13 (dd, J = 7.5, 7.5 Hz, 2H), 7.08 (d, J = 7.5 Hz, 2H), 3.47 – 3.37 (m, 2H), 3.07 – 2.97 (m, 2H), 2.22 (t, J = 7.5 Hz, 2H), 1.82 (s, 3H), 1.56 (br s, 1H), 1.45 – 1.39 (m, 2H), 1.32 – 1.25 (m, 2H), 0.84 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 144.5, 141.8, 130.5, 127.7, 126.6, 126.0, 64.2, 43.0, 35.4, 32.9, 32.9, 20.5, 14.1 |
| HRMS (ESI) | m/z calcd for C₂₀H₂₆N [M + H]⁺ 280.2060; found 280.2057 |
| IR (ATR) νmax | 3323, 3056, 2953, 1601, 1482, 1448, 1375, 1204, 753 cm⁻¹ |
| Identifier | 91 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.40 (d, J = 7.5 Hz, 1H), 7.17 (dd, J = 7.5, 7.5 Hz, 1H), 7.10 (dd, J = 7.5, 7.5 Hz, 1H), 7.05 (d, J = 7.5 Hz, 1H), 2.80 – 2.69 (m, 2H), 2.50 – 2.45 (m, 1H), 2.22 – 2.17 (m, 1H), 2.08 – 2.03 (m, 1H), 1.92 – 1.85 (m, 1H), 1.84 – 1.77 (m, 1H), 1.68 – 1.63 (m, 1H), 1.44 – 1.39 (m, 2H), 1.39 (br s, 1H), 1.38 (s, 3H), 1.34 – 1.28 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 142.9, 137.5, 128.9, 126.3, 126.0, 125.9, 55.1, 42.3, 34.8, 33.1, 31.5, 30.3, 20.6 (overlapped with 2C), 14.0 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1904 |
| IR (ATR) νmax | 3328, 3061, 2955, 1604, 1485, 1368, 1166, 759, 700 cm⁻¹ |
| Identifier | 92 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.38 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 2.39 (ddd, J = 11.0, 7.0, 7.0 Hz, 1H), 2.19 (ddd, J = 11.0, 7.0, 7.0 Hz, 1H), 1.74 – 1.61 (m, 2H), 1.57 (br s, 1H), 1.44 (s, 3H), 1.42 – 1.36 (m, 2H), 1.33 – 1.26 (m, 2H), 1.26 – 1.19 (m, 2H), 1.17 – 1.09 (m, 1H), 1.07 – 0.97 (m, 1H), 0.86 (t, J = 7.0 Hz, 3H), 0.83 (t J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.1, 127.9, 126.2, 125.9, 58.3, 43.3, 42.2, 33.1, 26.1, 24.9, 23.2, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₈N [M + H]⁺ 234.2216; found 234.2217 |
| IR (ATR) νmax | 3335, 3086, 2956, 1691, 1494, 1375, 1178, 763, 699 cm⁻¹ |
| Identifier | 93 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.48 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 2.45 – 2.34 (m, 2H), 1.49 (br s, 1H), 1.47 – 1.40 (m, 2H), 1.36 – 1.28 (m, 2H), 1.24 (s, 3H), 1.19 (dddd, J = 8.5, 8.5, 5.5, 5.5 Hz, 1H), 0.87 (t, J = 7.5 Hz, 3H), 0.50 – 0.43 (m, 1H), 0.43 – 0.35 (m, 1H), 0.34 – 0.27 (m, 1H), 0.26 – 0.19 (m, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.6, 127.8, 126.7, 126.1, 58.1, 42.3, 33.2, 23.9, 22.4, 20.6, 14.0, 2.2, 0.6 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1904 |
| IR (ATR) νmax | 3334, 3081, 2957, 1601, 1491, 1376, 1143, 762, 700 cm⁻¹ |
| Identifier | 94 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.33 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 2.40 (ddd, J = 10.5, 7.0, 7.0 Hz, 1H), 2.10 (ddd, J = 10.5, 7.0, 7.0 Hz, 1H), 1.89 – 1.80 (m, 1H), 1.78 – 1.70 (m, 1H), 1.66 – 1.56 (m, 2H), 1.44 (dddd, J = 12.0, 12.0, 3.0, 3.0 Hz, 1H), 1.41 (s, 3H), 1.41 – 1.32 (m, 3H), 1.32 – 1.24 (m, 3H), 1.24 – 1.13 (m, 1H), 1.10 – 1.01 (m, 2H), 0.94 (dddd, J = 12.0, 12.0, 3.0, 3.0 Hz, 1H), 0.85 (t, J = 7.5 Hz, 3H), 0.88 – 0.79 (m, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.5, 127.6, 127.0, 125.7, 61.1, 50.3, 42.2, 33.3, 27.9, 27.7, 27.0, 26.9, 26.7, 20.6, 20.4, 14.1 |
| HRMS (ESI) | m/z calcd for C₁₈H₃₀N [M + H]⁺ 260.2373; found 260.2375 |
| IR (ATR) νmax | 3344, 3085, 2952, 1600, 1492, 1374, 1180, 759, 700 cm⁻¹ |
| Identifier | 95 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.24 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 4.02 (dd, J = 8.5, 5.5 Hz, 1H), 3.80 (s, 3H), 3.63 (s, 3H), 2.70 (dd, J = 15.5, 8.5 Hz, 1H), 2.59 (dd, J = 15.5, 5.5 Hz, 1H), 2.42 (ddd, J = 18.0, 11.5, 7.0 Hz, 1H), 2.41 (ddd, J = 18.0, 11.5, 7.0 Hz, 1H), 1.71 (br s, 1H), 1.46 – 1.37 (m, 2H), 1.35 – 1.23 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 172.4, 158.8, 134.9, 128.0, 113.8, 58.9, 55.2, 51.5, 47.1, 42.8, 32.2, 20.4, 13.9 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄NO₃ [M + H]⁺ 266.1751; found 266.1750 |
| IR (ATR) νmax | 3323, 3064, 2925, 1734, 1610, 1463, 1376, 1246, 1176, 831 cm⁻¹ |
| Identifier | 96 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.32 (d, J = 8.5 Hz, 2H), 6.92 (d, J = 8.5 Hz, 2H), 3.99 (dd, J = 6.5, 6.5 Hz, 1H), 3.82 (s, 3H), 2.85 (dd, J = 17.0, 6.5 Hz, 1H), 2.79 (dd, J = 17.0, 6.5 Hz, 1H), 2.54 (ddd, J = 19.0, 6.5, 3.0 Hz, 1H), 2.52 (ddd, J = 19.0, 6.5, 3.0 Hz, 1H), 1.56 – 1.46 (m, 2H), 1.38 – 1.26 (m, 2H), 0.88 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 159.7, 131.3, 128.0, 117.5, 114.3, 58.7, 55.2, 47.0, 31.4, 26.2, 20.2, 13.8 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₁N₂O [M + H]⁺ 233.1649; found 233.1649 |
| IR (ATR) νmax | 3323, 3064, 2927, 2248, 1611, 1512, 1463, 1375, 1246, 831 cm⁻¹ |
| Identifier | 97 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.19 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.81 (s, 3H), 3.42 (dd, J = 8.5, 6.0 Hz, 1H), 2.47 – 2.35 (m, 2H), 1.79 – 1.70 (m, 1H), 1.64 – 1.54 (m, 1H), 1.47 – 1.36 (m, 2H), 1.33 – 1.23 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H), 0.78 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 158.4, 136.2, 128.2, 113.5, 64.6, 55.2, 47.4, 32.3, 30.9, 20.5, 14.0, 10.8 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₄NO [M + H]⁺ 222.1853; found 222.1850 |
| IR (ATR) νmax | 3333, 3063, 2928, 1610, 1510, 1460, 1377, 1245, 1174, 828 cm⁻¹ |
| Identifier | 98 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.38 (d, J = 8.0 Hz, 2H), 6.84 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 2.21 (t, J = 7.0 Hz, 2H), 2.00 – 1.89 (m, 4H), 1.88 – 1.78 (m, 2H), 1.73 – 1.64 (m, 2H), 1.35 – 1.28 (m, 2H), 1.28 – 1.18 (m, 2H), 0.81 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.9, 127.9, 126.5, 126.0, 67.9, 43.1, 38.0, 33.0, 23.1, 20.5, 13.9 |
| HRMS (ESI) | m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1901 |
| IR (ATR) νmax | 3083, 2955, 1600, 1493, 1377, 1176, 763, 698 cm⁻¹ |
| Identifier | 99 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.44 (d, J = 8.0 Hz, 2H), 7.32 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 2.16 (t, J = 7.0 Hz, 2H), 1.92 – 1.77 (m, 4H), 1.67 – 1.54 (m, 4H), 1.53 – 1.45 (m, 2H), 1.38 – 1.30 (m, 2H), 1.30 – 1.20 (m, 2H), 0.83 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 147.5, 128.0, 126.2, 125.9, 57.2, 41.3, 36.2, 33.1, 26.0, 22.2, 20.5, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₆N [M + H]⁺ 232.2060; found 232.2061 |
| IR (ATR) νmax | 3083, 2927, 1600, 1494, 1444, 1377, 1152, 758, 698 cm⁻¹ |
| Identifier | 100 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.28 – 7.21 (m, 8H), 7.17 (dd, J = 7.5, 7.5 Hz, 2H), 7.11 (t, J = 7.5 Hz, 1H), 7.06 (dd, J = 7.5, 7.5 Hz, 2H), 6.63 (d, J = 7.5 Hz, 2H), 3.57 (s, 2H), 2.37 (t, J = 7.5 Hz, 2H), 1.53 (br s, 1H), 1.43 – 1.37 (m, 2H), 1.34 – 1.27 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 146.9, 137.2, 130.5, 129.1, 128.3, 128.0, 127.6, 127.7, 127.5, 126.2, 126.6, 126.2, 65.5, 42.6, 42.3, 32.7, 20.5, 14.1 |
| HRMS (ESI) | m/z calcd for C₂₄H₂₈N [M + H]⁺ 330.2216; found 330.2219 |
| IR (ATR) νmax | 3327, 3086, 2953, 1601, 1495, 1236, 741, 695 cm⁻¹ |
| Identifier | 101 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.33 (d, J = 9.0 Hz, 2H), 6.82 (d, J = 9.0 Hz, 2H), 3.81 (s, 3H), 2.77 (t, J = 7.5 Hz, 2H), 1.54 – 1.47 (m, 2H), 1.44 (s, 6H), 1.42 – 1.37 (m, 2H), 0.94 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 159.1, 132.9, 115.5, 113.8, 93.0, 81.7, 55.2, 50.3, 44.0, 32.6, 29.6, 20.6, 14.0 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₄NO [M + H]⁺ 246.1853; found 246.1853 |
| IR (ATR) νmax | 3327, 3087, 2928, 1605, 1508, 1496, 1377, 1244, 830, 696 cm⁻¹ |
| Identifier | 102 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.31 (d, J = 8.5 Hz, 1H), 7.24 – 7.19 (m, 2H), 3.67 (t, J = 4.0 Hz, 4H), 2.94 – 2.89 (m, 2H), 2.54 – 2.40 (m, 6H), 2.33 – 2.25 (m, 1H), 2.14 (ddd, J = 19.0, 9.0, 9.0 Hz, 1H), 2.10 – 2.00 (m, 2H), 1.98 – 1.94 (m, 1H), 1.67 – 1.57 (m, 2H), 1.57 – 1.40 (m, 4H), 1.33 (s, 6H), 0.91 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 221.0, 145.9, 137.5, 135.8, 126.7, 124.9, 123.8, 67.8, 59.3, 50.5, 48.0, 46.6, 44.3, 38.2, 35.8, 31.6, 29.7, 26.7, 25.6, 23.9, 23.8, 21.6, 13.8 |
| HRMS (ESI) | m/z calcd for C₂₅H₃₆NO₂ [M + H]⁺ 382.2741; found 382.2740 |
| IR (ATR) νmax | 3085, 2952, 1738, 1603, 1496, 1375, 1244, 1176, 1114, 698 cm⁻¹ |
| Identifier | 103 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 6.83 – 6.76 (m, 3H), 4.05 (q, J = 7.0 Hz, 2H), 3.88 (s, 3H), 3.87 (s, 3H), 3.72 (dd, J = 7.0, 7.0 Hz, 1H), 3.68 – 3.61 (m, 4H), 2.94 (dd, J = 14.5, 7.0 Hz, 1H), 2.61 (dd, J = 14.5, 7.0 Hz, 1H), 2.48 – 2.35 (m, 4H), 1.16 (t, J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 171.6, 148.7, 148.3, 131.5, 120.5, 111.3, 110.6, 67.1, 66.1, 60.3, 55.9, 55.8, 50.5, 38.5, 14.1 |
| HRMS (ESI) | m/z calcd for C₁₇H₂₆NO₅ [M + H]⁺ 324.1806; found 324.1804 |
| IR (ATR) νmax | 3053, 2955, 1732, 1605, 1513, 1463, 1255, 1114, 855 cm⁻¹ |
| Identifier | 104 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 (d, J = 8.0 Hz, 2H), 7.18 – 7.05 (m, 6H), 3.33 – 3.24 (m, 2H), 3.21 (t, J = 7.0 Hz, 2H), 3.15 – 3.07 (m, 2H), 2.45 (t, J = 7.0 Hz, 2H), 2.34 (s, 3H), 1.84 – 1.76 (m, 2H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 144.8, 140.8, 130.4, 128.3, 126.4, 125.7, 75.6, 54.0, 42.0, 36.9, 34.8, 22.4 |
| HRMS (ESI) | m/z calcd for C₁₉H₂₂N [M + H]⁺ 264.1747; found 264.1745 |
| IR (ATR) νmax | 3060, 2927, 1602, 1477, 1356, 1233, 1052, 752 cm⁻¹ |
| Identifier | 105 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.04 (s, 2H), 5.95 (br s, 1H), 4.54 (dd, J = 5.5, 5.5 Hz, 1H), 4.38 – 4.29 (m, 1H), 3.79 (dd, J = 9.0, 3.5 Hz, 1H), 3.69 (dd, J = 9.0, 3.0 Hz, 1H), 3.65 – 3.58 (m, 2H), 3.52 – 3.44 (m, 2H), 2.46 (d, J = 5.5 Hz, 2H), 2.24 (s, 6H), 2.03 (s, 3H), 1.72 (br s, 1H), 1.42 (s, 6H), 1.40 (d, J = 7.0 Hz, 3H), 1.20 (t, J = 7.0 Hz, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 169.4, 153.0, 143.0, 129.9, 126.4, 102.7, 73.8, 62.0, 54.9, 45.5, 45.3, 29.5, 29.5, 23.4, 17.7, 16.4, 15.3 |
| HRMS (ESI) | m/z calcd for C₂₂H₃₉N₂O₄ [M + H]⁺ 395.2905; found 395.2903 |
| IR (ATR) νmax | 3463, 3288, 3076, 2973, 1648, 1548, 1486, 1372, 1192 cm⁻¹ |
| Identifier | 106 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.33 (d, J = 7.5 Hz, 2H), 7.31 – 7.26 (m, 3H), 7.24 – 7.18 (m, 3H), 7.18 – 7.14 (m, 1H), 3.69 (q, J = 7.0 Hz, 1H), 3.63 (s, 3H), 3.12 (s, 2H), 2.31 (br s, 1H), 1.77 (s, 3H), 1.46 (d, J = 7.0 Hz, 3H), 1.41 (s, 9H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 174.9 (overlapped with 2C), 171.8 (overlapped with 2C), 147.8, 147.7, 147.1, 147.1, 140.3, 140.3, 128.3, 128.3, 128.0 (overlapped with 2C), 127.1, 127.0, 126.5 (overlapped with 2C), 126.4, 126.4, 126.0, 126.0, 125.3 (overlapped with 2C), 81.1 (overlapped with 2C), 62.4 (overlapped with 2C), 51.9 (overlapped with 2C), 46.2 (overlapped with 2C), 45.5, 45.4, 28.0 (overlapped with 2C), 27.9, 27.8, 18.7, 18.5 |
| HRMS (ESI) | m/z calcd for C₂₄H₃₂NO₄ [M + H]⁺ 398.2336; found 398.2327 |
| IR (ATR) νmax | 3333, 3058, 2977, 1734, 1601, 1487, 1368, 1236, 1157, 703 cm⁻¹ |
| NMR reporting qualifier | mixture of diastereoisomers |
| Identifier | 107 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.02 (s, 1H), 6.72 (d, J = 7.5 Hz, 1H), 6.65 (s, 1H), 6.62 (d, J = 7.5 Hz, 1H), 6.52 (s, 1H), 5.92 (s, 2H), 3.95 (q, J = 6.5 Hz, 1H), 3.91 – 3.86 (m, 2H), 3.66 (s, 3H), 2.75 – 2.61 (m, 4H), 2.25 (s, 3H), 2.16 (s, 3H), 1.74 – 1.67 (m, 4H), 1.55 (br s, 1H), 1.25 (d, J = 6.5 Hz, 3H), 1.21 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 178.3, 155.3, 147.6, 145.8, 134.6, 133.9, 133.2, 127.3, 124.4, 121.5, 112.8, 109.0, 108.1, 100.7, 67.9, 52.9, 51.7, 48.9, 42.1, 37.1, 36.1, 25.2, 25.1, 23.2, 19.0, 15.8 |
| HRMS (ESI) | m/z calcd for C₂₇H₃₈NO₅ [M + H]⁺ 456.2745; found 456.2747 |
| IR (ATR) νmax | 3322, 3061, 2950, 1728, 1613, 1488, 1389, 1249, 1194, 1139 cm⁻¹ |
| Identifier | 108 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 10.1 (br s, 2H), 7.79 (d, J = 7.5 Hz, 2H), 7.46 (d, J = 7.5 Hz, 2H), 7.40 – 7.34 (m, 3H), 7.23 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 3.60 – 3.54 (m, 2H), 1.73 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 139.3, 131.1, 130.5, 129.0, 128.8, 128.6, 128.4, 126.6, 62.6, 46.9, 26.1 |
| HRMS (ESI) | m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1589 |
| IR (ATR) νmax | 3100 – 2400 (br), 3041, 2986, 1588, 1484, 1281, 756, 711 cm⁻¹ |
| Identifier | 109 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.54 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 2.50 – 2.30 (m, 4H), 1.56 – 1.47 (m, 4H), 1.45 – 1.37 (m, 2H), 1.33 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 150.0, 127.8, 126.0, 125.8, 59.9, 47.3, 27.0, 25.1, 24.2 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₂N [M + H]⁺ 204.1747; found 204.1745 |
| IR (ATR) νmax | 3084, 2929, 1598, 1491, 1443, 1374, 1181, 760, 698 cm⁻¹ |
| Identifier | 110 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.10 (d, J = 8.5 Hz, 2H), 6.84 (dd, J = 8.5 Hz, 2H), 3.79 (s, 3H), 2.67 – 2.57 (m, 1H), 1.53 (dt, J = 7.5, 7.5 Hz, 2H), 1.31 – 1.22 (m, 2H), 1.20 (d, J = 7.0 Hz, 3H), 1.21 – 1.07 (m, 2H), 0.85 (t J = 7.0 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 157.5, 140.1, 127.8, 113.5, 55.2, 39.0, 38.3, 29.9, 22.8, 22.5, 14.1 |
| Identifier | 111 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.34 – 7.28 (m, 4H), 7.20 – 7.15 (m, 1H), 3.97 – 3.90 (m, 2H), 3.33 – 3.23 (m, 2H), 1.73 – 1.64 (m, 1H), 1.37 – 1.30 (m, 4H), 1.28 (s, 6H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 149.0, 127.9, 126.2, 125.5, 68.7, 46.7, 39.9, 28.0, 24.8 |
| Identifier | 112 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.81 (d, J = 7.5 Hz, 1H), 7.53 (dd, J = 7.5, 7.5 Hz, 1H), 7.43 (dd, J = 7.5, 7.5 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 3.45 – 3.40 (m, 2H), 1.75 – 1.67 (m, 2H), 1.49 (s, 6H), 1.46 – 1.38 (m, 2H), 0.97 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 167.5, 151.5, 131.4, 131.0, 127.9, 123.4, 120.5, 62.7, 39.4, 31.5, 26.0, 20.6, 13.9 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₀NO [M + H]⁺ 218.1540; found 218.1540 |
| IR (ATR) νmax | 3056, 2957, 1683, 1613, 1495, 1467, 1388, 753, 695 cm⁻¹ |
| Identifier | 113 |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 7.41 – 7.36 (m, 4H), 7.34 – 7.29 (m, 1H), 3.26 (ddd, J = 20.5, 8.5, 6.5 Hz, 1H), 3.02 (d, J = 14.5 Hz, 1H), 2.99 (d, J = 14.5 Hz, 1H), 2.92 (ddd, J = 20.5, 8.5, 6.5 Hz, 1H), 1.85 (s, 3H), 1.57 – 1.45 (m, 2H), 1.34 – 1.26 (m, 2H), 0.87 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 167.5, 142.0, 128.7, 127.6, 125.4, 58.8, 53.6, 40.5, 30.6, 23.2, 20.4, 13.6 |
| HRMS (ESI) | m/z calcd for C₁₄H₂₀NO [M + H]⁺ 218.1540; found 218.1539 |
| IR (ATR) νmax | 3060, 2957, 1740, 1602, 1497, 1447, 1378, 1244, 762, 699 cm⁻¹ |
| ¹H NMR monitoring, conditions | PAZ (1.3 mg), 1 (47.4 mg, 0.401 mmol, 1 equiv), 2 (44.1 mg, 0.603 mmol, 1.5 equiv), and CH₃CN (1.0 mL) in a 10 mL Schlenk tube under N₂; 415 nm LEDs, <35 °C. At each indicated time point, a 50 μL aliquot was transferred to a J Young NMR tube, and the solvent was removed under vacuum, followed by 1,1,2,2-tetrachloroethane (50 μL of a 0.4 M solution in CDCl₃) as an internal standard and CDCl₃ (2.0 mL) |
|---|---|
| ¹H NMR monitoring, light on–off sequence | The product yield increased under irradiation, remained essentially unchanged in the dark, and increased again when irradiation was resumed |