| Identifier | 2aa |
|---|---|
| TLC (40 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.20; 2aa = 0.26 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.57–7.55 (m, 2H), 7.39–7.33 (m, 4H), 3.84 (s, 6H), 3.36 (m, 1H), 3.28 (s, 1H), 1.63–1.54 (m, 1H), 1.51–1.43 (m, 1H), 0.76 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.0, 168.7, 138.6, 129.0, 128.4, 126.1, 107.9, 76.8, 60.7, 53.6, 53.3, 18.8, 12.4 |
| IR (thin film) | 3210, 2980, 1750, 1710, 1560, 1490, 1370, 1245, 1150 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₅H₂₀NO₆ [M+H]⁺ 310.1291, found 310.1296 |
| Melting point | 110–117 °C |
Dylan C. Keane, Abdullah S. Alshreimi, Laura Alonso, Oishik Sarkar, Lam Minh Uyen Phan, Benjamin Stageberg, Donald J. Wink, Laura L. Anderson. “Synthesis of 5-aminoisoxazolidines from azetidine nitrones via formal ring expansion.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15007888/v1
| Identifier | 2ab |
|---|---|
| TLC (40 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.20; 2ab = 0.67 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.59–7.57 (m, 2H), 7.35–7.29 (m, 3H), 6.88–6.87 (m, 3H), 6.56–6.55 (d, J = 8.5 Hz, 2H), 4.78 (s, 1H), 3.89 (s, 3H), 3.88 (s, 3H), 3.34 (dd, J = 9.4, 5.2 Hz, 1H), 2.19 (t, 3H), 1.70–1.62 (m, 1H), 1.49–1.39 (m, 1H), 0.87 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.5, 169.7, 139.8, 138.0, 129.2, 128.6, 128.4, 128.3, 127.2, 116.9, 99.5, 77.4, 63.3, 53.6, 53.5, 20.4, 18.8, 12.6 |
| IR (thin film) | 3395, 3243, 2953, 2934, 2359, 1739, 1720, 1616, 1589, 1517, 1494 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₂H₂₇N₂O₅ [M+H]⁺ 399.1920, found 399.1923 |
| Melting point | 156–158 °C |
| Identifier | 2ac |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.18; 2ac = 0.60 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.55–7.53 (m, 2H), 7.36–7.33 (m, 3H), 7.30 (d, J = 8.7 Hz, 2H), 6.88 (s, 1H), 6.67 (d, J = 8.6 Hz, 2H), 5.13 (s, 1H), 3.90 (s, 3H), 3.88 (s, 3H), 3.36 (dd, J = 9.5, 5.2 Hz, 1H), 1.69–1.62 (m, 1H), 1.49–1.41 (m, 1H), 0.87 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.3, 169.9, 145.5, 137.2, 129.0, 128.8, 127.0, 126.1 (q, J = 3.7 Hz), 124.8 (q, J = 268.8 Hz), 121.1 (q, J = 32.2 Hz), 116.5, 99.2, 77.2, 63.5, 53.8 (2C), 18.8, 12.6 |
| IR (thin film) | 3377, 3217, 2921, 2851, 1736, 1617, 1528, 1504, 1449, 1431, 1324 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₂H₂₄N₂O₅F₃ [M+H]⁺ 453.1637, found 453.1638 |
| Melting point | 123–125 °C |
| Identifier | 2ad |
|---|---|
| TLC (50 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.22; 2ad = 0.59 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.59–7.57 (m, 2H), 7.34–7.30 (m, 3H), 6.86 (s, 1H), 6.65–6.63 (d, J = 9.1 Hz, 2H), 6.60–6.59 (d, J = 9.2 Hz, 2H), 4.70 (s, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.68 (s, 3H), 3.33 (dd, J = 9.4, 5.3 Hz, 1H), 1.70–1.61 (m, 1H), 1.47–1.38 (m, 1H), 0.86 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.4, 169.8, 153.0, 138.1, 136.0, 128.6, 128.2, 127.2, 118.1, 114.2, 99.7, 77.4, 63.2, 55.5, 53.5 (2C), 18.8, 12.6 |
| IR (thin film) | 3377, 3200, 2943, 2829, 1754, 1731, 1511, 1451, 1435, 1408, 1386 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₂H₂₇N₂O₆ [M+H]⁺ 415.1869, found 415.1870 |
| Melting point | 161–165 °C |
| Identifier | 2ae |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.18; 2ae = 0.12 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.57–7.55 (m, 2H), 7.32–7.30 (m, 3H), 6.85 (s, 1H), 6.56–6.51 (m, 4H), 4.80 (bs, 1H), 4.66 (s, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 3.32 (dd, J = 9.4, 5.4 Hz, 1H), 1.67–1.60 (m, 1H), 1.46–1.39 (m, 1H), 0.85 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.4, 169.7, 148.9, 138.0, 135.9, 128.6, 128.3, 127.3, 118.3, 115.7, 99.8, 77.5, 63.2, 53.6 (2C), 18.8, 12.6 |
| IR (thin film) | 3409, 2955, 2359, 2342, 1727, 1513, 1436, 1382, 1292, 1241, 1217 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₁H₂₅N₂O₆ [M+H]⁺ 401.1713, found 401.1707 |
| Melting point | 81–85 °C |
| Identifier | 2af |
|---|---|
| TLC (40 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.20; 2af = 0.53 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.56–7.55 (m, 2H), 7.33–7.32 (m, 3H), 6.84 (s, 1H), 6.77–6.74 (m, 2H), 6.59–6.56 (m, 2H), 4.81 (s, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.33 (dd, J = 9.4, 5.3 Hz, 1H), 1.69–1.61 (m, 1H), 1.47–1.38 (m, 1H), 0.86 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.4, 169.9, 156.8 (d, J = 237.7 Hz), 138.5, 137.7, 128.7, 128.4, 127.2, 118.0 (d, J = 7.4 Hz), 115.2 (d, J = 22.2 Hz), 99.6, 77.3, 63.3, 53.6 (2C), 18.7, 12.6 |
| IR (thin film) | 3429, 2967, 2359, 1980, 1753, 1731, 1615, 1511, 1443, 1380, 1331 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₁H₂₄N₂O₅F [M+H]⁺ 403.1669, found 403.1667 |
| Melting point | 131–133 °C |
| Identifier | 2ag |
|---|---|
| TLC (40 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.20; 2ag = 0.62 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.52–7.51 (m, 2H), 7.33–7.31 (m, 3H), 7.10–7.09 (m, 1H), 6.89 (s, 1H), 6.82–6.79 (m, 1H), 6.69–6.66 (m, 1H), 6.49–6.47 (m, 1H), 4.74 (s, 1H), 3.88 (s, 6H), 3.38 (dd, J = 9.6, 5.2 Hz, 1H), 2.33 (s, 3H), 1.76–1.69 (m, 1H), 1.51–1.43 (m, 1H), 0.90 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.5, 169.5, 140.2, 137.7, 130.0, 128.6, 128.3, 127.0, 126.3, 123.7, 118.8, 116.9, 99.4, 77.5, 63.7, 53.6, 53.5, 18.9, 17.6, 12.6 |
| IR (thin film) | 3449, 3242, 2930, 2359, 1748, 1725, 1609, 1591, 1518, 1486, 1437 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₂H₂₇N₂O₅ [M+H]⁺ 399.1920, found 399.1922 |
| Melting point | 172–175 °C |
| Identifier | 2ah |
|---|---|
| TLC (40 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.20; 2ah = 0.74 |
| ¹H NMR (500 MHz, CDCl₃) | 7.46–7.44 (m, 2H), 7.32–7.28 (m, 3H), 7.06 (d, J = 2.8 Hz, 1H), 7.03 (s, 1H), 6.58 (d, J = 9.1 Hz, 1H), 6.48 (dd, J = 9.1, 2.8 Hz, 1H), 5.12 (s, 1H), 3.90 (s, 3H), 3.89 (s, 3H), 3.66 (s, 3H), 3.40 (dd, J = 9.5, 5.3 Hz, 1H), 1.76–1.68 (m, 1H), 1.57–1.48 (m, 1H), 0.91 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.4, 168.4, 152.7, 137.4, 133.7, 128.6, 128.4, 127.1, 118.5, 117.8, 113.7, 111.5, 99.7, 77.5, 63.5, 55.7, 53.6, 53.5, 18.8, 12.6 |
| IR (thin film) | 3378, 3199, 2953, 2829, 1753, 1731, 1512, 1451, 1436, 1408, 1384 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₂H₂₆N₂O₆Br [M+H]⁺ 493.0974, found 493.0981 |
| Melting point | 153–156 °C |
| Identifier | 2ai |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.18; 2ai = 0.41 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.57–7.55 (m, 2H), 7.32–7.31 (m, 3H), 6.90 (s, 1H), 6.40 (s, 1H), 6.29 (s, 2H), 4.74 (s, 1H), 3.89 (s, 3H), 3.88 (s, 3H), 3.34 (dd, J = 9.4, 5.4 Hz, 1H) 2.12 (s, 6H), 1.68–1.60 (m, 1H), 1.48–1.39 (m, 1H), 0.86 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.5, 169.6, 142.3, 138.3, 138.0, 128.6, 128.2, 127.1, 121.2, 114.9, 99.4, 77.4, 63.4, 53.6, 53.5, 21.4, 18.8, 12.6 |
| IR (thin film) | 3412, 3225, 2960, 2360, 2342, 2050, 1980, 1754, 1729, 1602, 1523 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₃H₂₉N₂O₅ [M+H]⁺ 413.2076, found 413.2071 |
| Melting point | 158–160 °C |
| Identifier | 2aj |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.18; 2aj = 0.45 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.97 (d, J = 8.5 Hz, 1H), 7.84 (d, J = 8.1 Hz, 1H), 7.60–7.55 (m, 3H), 7.51–7.49 (m, 1H), 7.30–7.29 (m, 4H), 7.10–7.07 (m, 1H), 6.93 (s, 1H), 6.67 (d, J = 7.7 Hz, 1H), 5.65 (s, 1H), 3.92 (s, 3H), 3.91 (s, 3H), 3.45 (dd, J = 9.6, 5.0 Hz, 1H), 1.94–1.86 (m, 1H), 1.71–1.62 (m, 1H), 0.97 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.5, 169.7, 137.4, 136.9, 134.2, 129.0, 128.6, 128.3, 127.0, 126.0, 125.6, 125.4, 124.8, 119.7, 119.5, 113.4, 99.8, 77.6, 63.9, 53.7, 53.6, 19.0, 12.7 |
| IR (thin film) | 3459, 3241, 2957, 1745, 1583, 1533, 1485, 1445, 1407, 1336, 1313 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₅H₂₇N₂O₅ [M+H]⁺ 435.1920, found 435.1920 |
| Melting point | 163–166 °C |
| Identifier | 2ak |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1a = 0.18; 2ak = 0.41 |
| ¹H NMR (500 MHz, CDCl₃) | δ 7.67–7.63 (m, 3H), 7.61 (d, J = 8.8 Hz, 1H), 7.46 (d, J = 8.3 Hz, 1H), 7.35–7.29 (m, 4H), 7.23–7.20 (m, 1H), 7.01–6.98 (m, 2H), 6.94 (s, 1H), 5.05 (s, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 3.44 (dd, J = 9.4, 5.4 Hz, 1H), 1.75–1.69 (m, 1H), 1.55–1.49 (m, 1H), 0.91 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.5, 169.8, 140.0, 137.7, 134.3, 128.8, 128.5 (2C), 128.2, 127.5, 127.3, 126.6, 126.1, 123.0, 119.3, 111.8, 99.6, 77.4, 63.5, 53.7 (2C), 18.9, 12.7 |
| IR (thin film) | 3363, 3220, 2952, 2879, 1739, 1632, 1605, 1529, 1492, 1475, 1447 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₅H₂₇N₂O₅ [M+H]⁺ 435.1920, found 435.1916 |
| Melting point | 136–138 °C |
| Identifier | 2ca |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1c = 0.20; 2ca = 0.73 |
| ¹H NMR (500 MHz, CDCl₃) | 7.73 (m, 2H), 7.49–7.47 (m, 2H), 7.41 (m, 2H), 7.36–7.33 (m, 1H), 7.26–7.25 (m, 3H), 7.08 (s, 1H), 6.91 (d, J = 8.3 Hz, 2H), 6.64 (d, J = 8.5 Hz, 2H), 5.07 (s, 1H), 3.76 (s, 3H), 3.00 (m, 1H), 2.22 (s, 3H), 1.96–1.87 (m, 1H), 1.87–1.78 (m, 1H), 0.92 (t, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 172.6, 142.4, 140.0, 139.0, 129.2, 128.4, 128.3, 128.1, 128.0, 127.6, 127.3 (2C), 117.1, 99.7, 76.6, 70.3, 53.2, 20.4, 20.2, 13.1 |
| IR (thin film) | 3414, 2922, 1713, 1616, 1515, 1491, 1447, 1434, 1301, 1249, 1211 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₆H₂₉N₂O₃ [M+H]⁺ 417.2178, found 417.2178 |
| Melting point | 48–51 °C |
| Identifier | 2da |
|---|---|
| TLC (40 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1d = 0.19; 2da = 0.71 |
| ¹H NMR (500 MHz, CDCl₃) | 7.65–7.63 (m, 2H), 7.39–7.33 (m, 3H), 6.90 (d, J = 8.3 Hz, 2H), 6.78 (s, 1H), 6.58 (d, J = 8.5 Hz, 2H), 4.87 (s, 1H), 4.46 (q, J = 7.2 Hz, 2H), 2.80 (dd, J = 9.0, 5.7 Hz, 1H), 2.21 (s, 3H), 1.77–1.68 (m, 1H), 1.61–1.52 (m, 1H), 1.42 (t, J = 7.2 Hz, 3H), 0.89 (t, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 167.3, 139.5, 137.6, 129.3, 128.8, 128.7, 128.6, 127.8, 124.5 (q, J = 282.1 Hz), 117.1, 99.3, 76.0 (q, J = 28.7 Hz), 63.8, 63.3, 20.4, 19.0, 14.0, 12.6 |
| IR (thin film) | 3428, 3251, 2921, 1734, 1711, 1617, 1592, 1519, 1448, 1392, 1373 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₂₂H₂₆N₂O₃F₃ [M+H]⁺ 423.1896, found 423.1898 |
| Melting point | 98–104 °C |
| Identifier | 2ba |
|---|---|
| ¹H NMR (500 MHz, CDCl₃) | δ 6.94 (s, 1H), 3.75 (s, 3H), 3.73 (s, 3H), 3.54–3.48 (m, 1H), 3.40–3.34 (m, 1H), 3.10 (q, J = 7.3 Hz, 1H), 1.36 (s, 3H), 1.11 (t, J = 7.1 Hz, 3H), 0.99 (d, J = 7.3 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 170.0, 168.3, 108.5, 76.0, 56.5, 53.4, 52.9, 52.4, 17.1, 15.3, 10.2 |
| IR (thin film) | 3239, 2978, 2955, 2887, 1735, 1455, 1438, 1384, 1330, 1282, 1226 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₁H₁₉NO₆Na [M+Na]⁺ 284.1109, found 284.1110 |
| Identifier | 2bb |
|---|---|
| TLC (30 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1b = 0.01; 2bb = 0.30 |
| ¹H NMR (500 MHz, CDCl₃, major diastereomer) | δ 7.01 (s, 1H), 6.92–6.86 (m, 4H), 3.83 (s, 3H), 3.82 (s, 3H), 3.34 (q, J = 7.5 Hz, 1H), 1.53 (s, 3H), 1.14 (d, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃, major diastereomer) | δ 170.2, 169.0, 157.8 (d, J = 237.6 Hz), 139.4, 120.4 (d, J = 7.8 Hz), 115.6 (d, J = 22.1 Hz), 97.5, 77.0, 53.7, 53.5, 53.0, 19.6, 10.4 |
| ¹H NMR (500 MHz, CDCl₃, minor diastereomer, diagnostic peaks) | δ 3.78 (s, 3H), 1.40 (s, 3H), 1.07 (d, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃, minor diastereomer, diagnostic peaks) | δ 98.8, 53.2, 17.8, 12.2 |
| IR (thin film) | 3420, 3217, 2984, 2956, 1730, 1507, 1455, 1438, 1378, 1286, 1206 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₅H₂₀N₂O₅F [M+H]⁺ 327.1358, found 327.1356 |
| Identifier | 2bc |
|---|---|
| TLC (30 % EtOAc:hexanes; KMnO₄ stain), Rf | 1b = 0.01; 2bc = 0.30 |
| ¹H NMR (500 MHz, CDCl₃, major diastereomer) | δ 7.37–7.28 (m, 5H), 6.61 (s, 1H), 3.94–3.87 (m, 2H), 3.80 (s, 3H), 3.78 (s, 3H), 3.21 (q, J = 7.5 Hz, 1H), 2.19 (brs, 1H), 1.47 (s, 3H), 1.03 (d, J = 7.5 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃, major diastereomer) | δ 170.3, 170.1, 140.8, 128.5, 127.9, 127.0, 98.9, 77.4, 53.5 (2C), 52.2, 45.0, 20.2, 10.6 |
| ¹H NMR (500 MHz, CDCl₃, minor diastereomer, diagnostic peaks) | δ 7.25–7.23 (m, 5H), 6.51 (s, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 3.26 (q, J = 7.4 Hz, 1H), 1.31 (s, 3H) |
| ¹³C NMR (125 MHz, CDCl₃, minor diastereomer, diagnostic peaks) | δ 170.0, 169.2, 140.6, 128.5, 128.1, 127.0, 100.5, 53.2, 45.6, 18.4, 11.7 |
| IR (thin film) | 3351, 3229, 3029, 2954, 2850, 1726, 1496, 1453, 1437, 1286, 1228 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₆H₂₃N₂O₅ [M+H]⁺ 323.1612, found 323.1607 |
| Identifier | 2bd |
|---|---|
| TLC (30 % EtOAc:hexanes; KMnO₄ stain), Rf | 1b = 0.01; 2bd = 0.30 |
| ¹H NMR (500 MHz, CDCl₃, major diastereomer) | δ 6.50 (s, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 3.12 (q, J = 7.5 Hz, 1H), 2.71–2.66 (m, 1H), 2.57–2.52 (m, 1H), 1.80 (brs, 1H), 1.45–1.41 (m, 2H), 1.39 (s, 3H), 1.34–1.29 (m, 2H), 0.97 (d, J = 7.5 Hz, 3H), 0.91 (t, J = 7.2 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃, major diastereomer) | δ 170.4 (2C), 96.0, 77.5, 53.3 (2C), 52.0, 40.3, 32.8, 20.5, 20.0, 14.0, 10.6 |
| ¹H NMR (500 MHz, CDCl₃, minor diastereomer, diagnostic peaks) | δ 6.41 (s, 1H), 3.51–3.48 (m, 1H), 3.45–3.43 (m, 1H), 0.88 (t, J = 7.2 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃, minor diastereomer, diagnostic peaks) | δ 170.1, 169.2, 53.3, 53.2, 41.2, 33.1, 20.4, 18.1, 13.8, 11.7 |
| IR (thin film) | 3360, 3233, 2956, 2933, 2873, 1728, 1456, 1438, 1381, 1288, 1228 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₃H₂₅N₂O₅ [M+H]⁺ 289.1766, found 289.1763 |
| Identifier | 2be’ |
|---|---|
| TLC (30 % EtOAc:hexanes; KMnO₄ stain), Rf | 1b = 0.01; 2be’ = 0.06 |
| ¹H NMR (500 MHz, CDCl₃) | δ 6.71 (s, 1H), 3.78 (s, 3H), 3.75 (s, 3H), 3.57–3.52 (m, 4H), 3.42 (q, J = 7.4 Hz, 1H), 2.57–2.55 (m, 2H), 2.46–2.30 (m, 2H), 1.09 (s, 3H), 0.96 (d, J = 7.4 Hz, 3H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 169.2, 168.6, 99.6, 78.6, 67.2, 53.4, 53.2, 48.6, 45.7, 12.4, 10.8 |
| IR (thin film) | 3265, 2955, 2892, 2855, 1748, 1732, 1453, 1437, 1384, 1266, 1243 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₃H₂₃N₂O₆ [M+H]⁺ 303.1563, found 303.1556 |
| Melting point | 85–88 °C |
| Identifier | 2ea’ |
|---|---|
| TLC (60 % EtOAc:hexanes; KMnO₄ stain), Rf | 1e = 0.37; 2ea’ = 0.44 |
| ¹H NMR (500 MHz, CDCl₃) | δ 6.91 (s, 1H), 3.77, (s, 3H), 3.72 (s, 3H), 3.57–3.40 (m, 4H), 3.30 (dd, J = 12.1, 6.2 Hz, 1H), 2.63–2.51 (m, 2H), 2.44–2.36 (m, 2H), 1.80–1.77 (m, 1H), 1.65–1.62 (m, 1H), 1.58–1.47 (m, 3H), 1.37–1.26 (m, 2H), 1.08–1.00 (m, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 168.8, 168.1, 96.6, 78.5, 67.2, 53.4, 53.3, 48.6, 45.2, 24.9, 24.0, 21.7, 21.5 |
| IR (thin film) | 3266, 2950, 2858 1747, 1731, 1435, 1376, 1360, 1329, 1262, 1245 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₅H₂₅N₂O₆ [M+H]⁺ 329.1718, found 329.1713 |
| Melting point | 62–65 °C |
| Identifier | 2eb’ |
|---|---|
| TLC (30 % EtOAc:hexanes; KMnO₄ stain), Rf | 1e = 0.02; 2eb’ = 0.34 |
| ¹H NMR (500 MHz, CDCl₃, 50 °C) | δ 6.88 (s, 1H), 3.76 (s, 3H), 3.72 (s, 3H), 3.36 (dd, J = 12.1, 6.1 Hz, 1H), 2.55 (m, 2H), 2.35 (m, 2H), 1.80–1.78 (m, 1H), 1.66–1.53 (m, 4H), 1.50–1.33 (m, 8H), 1.10–1.02 (m, 1H) |
| ¹³C NMR (125 MHz, CDCl₃, 50 °C) | δ 168.9, 168.5, 97.3, 78.9, 53.2, 53.0, 49.4, 46.1, 26.3, 25.4, 25.1, 24.2, 21.8, 21.7 |
| IR (thin film) | 3265, 2934, 2854, 2807, 1750, 1731, 1435, 1357, 1245, 1225, 1203 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₆H₂₇N₂O₅ [M+H]⁺ 327.1920, found 327.1920 |
| Melting point | 98–102 °C |
| Identifier | 2ec’ |
|---|---|
| TLC (60 % EtOAc:hexanes; UV₂₅₄ lamp), Rf | 1e = 0.37; 2ec’ = 0.70 |
| ¹H NMR (500 MHz, CDCl₃) | δ 6.99 (s, 1H), 6.98 (d, J = 8.0 Hz, 2H), 6.80 (d, J = 8.4 Hz, 2H), 3.81 (s, 3H), 3.71 (s, 3H), 3.54 (s, 1H), 3.25 (dd, J = 11.4, 5.8 Hz, 1H), 2.33 (d, J = 13.9 Hz, 1H), 2.24 (s, 3H), 2.18–2.11 (m, 1H), 1.69–1.64 (m, 3H), 1.54–1.47 (m, 2H), 1.31–1.25 (m, 1H) |
| ¹³C NMR (125 MHz, CDCl₃) | δ 169.5, 168.4, 141.4, 129.7 (2C), 118.1, 95.5, 78.4, 53.7, 53.3, 29.8, 24.6, 23.4, 21.5, 20.6 |
| IR (thin film) | 3499, 3371, 3001, 2936, 2863, 1732, 1616, 1514, 1448, 1357, 1264 cm⁻¹ |
| HRMS (ESI) | m/z calcd. for C₁₈H₂₅N₂O₅ [M+H]⁺ 349.1761, found 349.1763 |
| Melting point | 78–80 °C |
| Identifier | 2aa |
|---|---|
| Method | Single-crystal X-ray diffraction |
| Chemical formula | C₁₅H₁₉NO₆ |
| Formula weight | 309.31 g/mol |
| Temperature | 298(2) K |
| Wavelength | 0.71073 Å |
| Crystal size | 0.162 × 0.183 × 0.422 mm |
| Crystal system | monoclinic |
| Space group | P 1 2₁/c 1 |
| Unit cell dimensions | a = 10.042(2) Å, α = 90°; b = 6.7594(16) Å, β = 96.934(3)°; c = 23.329(6) Å, γ = 90° |
| Volume | 1571.9(6) ų |
| Z | 4 |
| Density (calculated) | 1.307 g/cm³ |
| Absorption coefficient | 0.102 mm⁻¹ |
| F(000) | 656 |
| Theta range for data collection | 1.76 to 24.79° |
| Index ranges | −11 ≤ h ≤ 11, −7 ≤ k ≤ 7, −27 ≤ l ≤ 27 |
| Reflections collected | 14976 |
| Independent reflections | 2688 [R(int) = 0.0447] |
| Coverage of independent reflections | 100.0 % |
| Max. and min. transmission | 0.9840 and 0.9580 |
| Data/restraints/parameters | 2688/0/207 |
| Goodness-of-fit on F² | 0.875 |
| Final R indices (1914 data; I > 2σ(I)) | R1 = 0.0448, wR2 = 0.1266 |
| Final R indices (all data) | R1 = 0.0724, wR2 = 0.1485 |
| Absolute structure parameter | 0.0(10) |
| Largest diff. peak and hole | 0.295 and −0.197 e Å⁻³ |
| R.M.S. deviation from mean | 0.037 e Å⁻³ |
| Identifier | 2be’ |
|---|---|
| Method | Single-crystal X-ray diffraction |
| Chemical formula | C₁₃H₂₂N₂O₆ |
| Formula weight | 302.32 g/mol |
| Temperature | 296(2) K |
| Wavelength | 0.71073 Å |
| Crystal size | 0.100 × 0.200 × 0.300 mm |
| Crystal system | monoclinic |
| Space group | P 1 2₁/n 1 |
| Unit cell dimensions | a = 11.0754(18) Å, α = 90°; b = 10.1126(16) Å, β = 108.776(2)°; c = 14.285(2) Å, γ = 90° |
| Volume | 1514.8(4) ų |
| Z | 4 |
| Density (calculated) | 1.326 g/cm³ |
| Absorption coefficient | 0.105 mm⁻¹ |
| F(000) | 648 |
| Theta range for data collection | 2.04 to 26.37° |
| Index ranges | −13 ≤ h ≤ 13, −12 ≤ k ≤ 12, −17 ≤ l ≤ 17 |
| Reflections collected | 15920 |
| Independent reflections | 3100 [R(int) = 0.0368] |
| Coverage of independent reflections | 99.9 % |
| Max. and min. transmission | 0.9900 and 0.9690 |
| Data/restraints/parameters | 3100/0/194 |
| Goodness-of-fit on F² | 0.917 |
| Δ/σmax | 0.003 |
| Final R indices (2306 data; I > 2σ(I)) | R1 = 0.0492, wR2 = 0.1402 |
| Final R indices (all data) | R1 = 0.0685, wR2 = 0.1592 |
| Largest diff. peak and hole | 0.694 and −0.623 e Å⁻³ |
| R.M.S. deviation from mean | 0.046 e Å⁻³ |
| Identifier | 2 |
|---|---|
| ¹H–¹H nOe correlation data | Image data were not transcribed |
| Identifier | 2 |
|---|---|
| ¹H and ¹³C NMR spectra | Image data were not transcribed |