119205-38-8
基本信息
3-氨基-4,5,6,7-四氢苯并[B]噻吩-2-羧酸甲酯
methyl 3-amino-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxylate
Ethyl 3-amino-3a,4,5,6,7,7a-hexahydrobenzo[b]thiophene-2-carboxylate
3-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
Benzo[b]thiophene-2-carboxylic acid, 3-amino-4,5,6,7-tetrahydro-, methyl ester
3-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester ,97%
物理化学性质
| 熔点 | 70-73 °C |
| 沸点 | 414.3±45.0 °C(Predicted) |
| 密度 | 1.273±0.06 g/cm3(Predicted) |
| 储存条件 | 2-8°C(protect from light) |
| 酸度系数(pKa) | 2.24±0.20(Predicted) |
| 外观 | White to off-white Solid |
制备方法
![Acetic acid, 2-[(2-cyano-1-cyclohexen-1-yl)thio]-, methyl ester](/CAS/20210305/GIF/1263199-68-3.gif)
1263199-68-3
119205-38-8
以甲基-S-(2-氰基环己-1-烯基)磺酸乙酯（9）（0.17 g，0.78 mmol）为原料，将其与新蒸馏的无水THF（3 mL）混合。随后加入叔丁醇钾（0.09 g，0.78 mmol），并将反应混合物加热回流30分钟。反应进程通过薄层色谱法（TLC）监测（洗脱液：石油醚/乙酸乙酯，5:1）。反应完成后，将混合物在减压下浓缩，加入二氯甲烷（25 mL）溶解，并用蒸馏水（2×20 mL）洗涤，有机相经无水硫酸镁干燥。蒸发溶剂后，所得油状物在高真空（10^-1毫巴）下干燥。冷藏过夜后，得到淡黄色固体产物3-氨基-4,5,6,7-四氢苯并[b]噻吩-2-羧酸甲酯（135 mg，收率80%）。产物表征数据如下：熔点70-73℃；1H NMR (CDCl3) δ: 1.82 (m, 4H, H5, H6), 2.30 (m, 2H, H7), 2.67 (m, 2H, H4), 3.79 (s, 3H, COOCH3), 5.36 (br s, 2H, NH2); 13C NMR (CDCl3) δ: 21.9, 22.6 (2CH2, C5, C6), 23.1 (CH2, C4), 25.8 (CH2, C7), 51.1 (COOCH3), 97.3 (CAr), 126.2 (CAr), 143.5 (CAr), 152.6 (CAr), 165.4 (COOCH3); IR (KBr) ν: 768, 1072, 1095, 1130, 1198, 1263, 1300, 1342, 1448, 1493, 1568, 1604, 1668, 1734 (ester), 2858, 2933, 3361 (NH2), 3464 (NH2) cm^-1; MS (EI, 70 eV) m/z (%): 32 (80), 40 (10), 45 (10), 65 (10), 77 (15), 91 (15), 118 (15), 151 (65), 179 (90), 211 (M+, 100), 212 (M+H+, 10); HRMS-FAB: m/z [M+H]+ calcd for C10H13NO2S: 211.0667; found: 211.0745.
参考文献：
[1] Tetrahedron Letters, 2011, vol. 52, # 3, p. 401 - 403