119205-38-8
119205-38-8 結(jié)構(gòu)式
基本信息
3-氨基-4,5,6,7-四氫苯并[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%
物理化學(xué)性質(zhì)
制備方法
![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-氰基環(huán)己-1-烯基)磺酸乙酯（9）（0.17 g，0.78 mmol）為原料，將其與新蒸餾的無水THF（3 mL）混合。隨后加入叔丁醇鉀（0.09 g，0.78 mmol），并將反應(yīng)混合物加熱回流30分鐘。反應(yīng)進(jìn)程通過薄層色譜法（TLC）監(jiān)測（洗脫液：石油醚/乙酸乙酯，5:1）。反應(yīng)完成后，將混合物在減壓下濃縮，加入二氯甲烷（25 mL）溶解，并用蒸餾水（2×20 mL）洗滌，有機(jī)相經(jīng)無水硫酸鎂干燥。蒸發(fā)溶劑后，所得油狀物在高真空（10^-1毫巴）下干燥。冷藏過夜后，得到淡黃色固體產(chǎn)物3-氨基-4,5,6,7-四氫苯并[b]噻吩-2-羧酸甲酯（135 mg，收率80%）。產(chǎn)物表征數(shù)據(jù)如下：熔點(diǎn)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.
參考文獻(xiàn)：
[1] Tetrahedron Letters, 2011, vol. 52, # 3, p. 401 - 403