性质与稳定性:在常温常压下,该物质不会分解。
2-羟基烟酸是一种有机中间体。有文献报道,可以通过一步反应从3-溴-2-羟基吡啶或3-氰基-2-吡啶酮制备得到。
用途2-羟基烟酸是一种烟酸的类似物,并作为一种生长因子用于埃尔温菌(如梨和苹果花)的生长。
制备在0℃下,向无水四氢呋喃(THF,20 mL)中的3-溴-2-羟基吡啶(0.76 g,4.4 mmol,1.0当量)溶液中加入2 M i-PrMgCl·THF(2.2 mL,1.0当量)。将该透明溶液在相同温度下再搅拌5分钟,并在5分钟内滴加2.5 M 正丁基锂的己烷溶液(3.5 mL,2.0当量),同时保持温度低于-20℃。所得混合物在-20℃下继续搅拌0.5小时后,向其中加入干燥的CO2(0.20 g,1.0当量)。随后,在0.5小时内将该混合物加热至-20℃并滴加水(6 mL)淬灭反应。在-20℃以下条件下继续搅拌10分钟后,分离各相,并用水萃取一次。使所得悬浮液恢复到室温后,通过0.5×1 cm的硅胶垫填充,用10 mL乙酸乙酯洗脱。浓缩滤液并使用硅胶快速色谱纯化(洗脱液:石油醚/乙酸乙酯=10:1),最终得到2-羟基烟酸,为灰白色固体,收率为79%,熔点255-257℃。
应用2-羟基烟酸为白色至淡黄色粉末,可用作医药中间体。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
烟酸 | nicotinic acid | 59-67-6 | C6H5NO2 | 123.111 |
1,2-二氢-2-氧代-3-吡啶甲酰胺 | 2-hydroxynicotinamide | 10128-92-4 | C6H6N2O2 | 138.126 |
氧烟酸 | Nicotinic acid N-oxide | 2398-81-4 | C6H5NO3 | 139.111 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
2-氧代-1,2-二氢-3-吡啶羧酸甲酯 | methyl 2-hydroxynicotinate | 10128-91-3 | C7H7NO3 | 153.137 |
1,2-二氢-2-氧代-3-吡啶羧酸乙酯 | 2-hydroxyl nicotinic acid ethyl ester | 27805-12-5 | C8H9NO3 | 167.164 |
5-溴-2-羟基烟酸 | 5-bromo-2-hydroxynicotinic acid | 104612-36-4 | C6H4BrNO3 | 218.007 |
—— | 1,2-dihydro-2-oxo-3,5-pyridinedicarboxylic acid | 95797-09-4 | C7H5NO5 | 183.12 |
2-羟基-5-碘烟酸 | 2-hydroxy-5-iodonicotinic acid | 390360-97-1 | C6H4INO3 | 265.007 |
5-氯-2-羟基烟酸 | 5-chloro-2-hydroxynicotinic acid | 38076-80-1 | C6H4ClNO3 | 173.556 |
—— | propan-2-yl 2-oxo-1,2-dihydropyridine-3-carboxylate | —— | C9H11NO3 | 181.191 |
1-甲基-2-氧代-1,2-二氢吡啶-3-羧酸 | 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 15506-18-0 | C7H7NO3 | 153.137 |
—— | 1,2-dihydro-2-oxo-3-pyridinecarboxylic acid, t-butyl ester | 95797-06-1 | C10H13NO3 | 195.218 |
2-羟基-3-吡啶甲醛 | 2-hydroxynicotinaldehyde | 36404-89-4 | C6H5NO2 | 123.111 |
—— | butyl 2-oxo-1,2-dihydropyridine-3-carboxylate | —— | C10H13NO3 | 195.218 |
3-(羟基甲基)-2(1H)-吡啶酮 | 3-(hydroxymethyl)pyridin-2(1H)-one | 42463-41-2 | C6H7NO2 | 125.127 |
2-氧代-5-碘-1,2-二氢-3-吡啶甲酸甲酯 | methyl 2-hydroxy-5-iodopyridine-3-carboxylate | 116387-40-7 | C7H6INO3 | 279.034 |
5-溴-2-羟基烟酸甲酯 | methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate | 120034-05-1 | C7H6BrNO3 | 232.034 |
烟酸 | nicotinic acid | 59-67-6 | C6H5NO2 | 123.111 |
—— | 1-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 141605-22-3 | C8H9NO3 | 167.164 |
1-甲基-2-氧-1,2-二氢吡啶-3-羧酸甲酯 | methyl 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate | 67367-27-5 | C8H9NO3 | 167.164 |
—— | 1-(difluoromethyl) -2-oxo-1,2-dihydropyridine-3-carboxylic acid | 1129458-32-7 | C7H5F2NO3 | 189.118 |
—— | 1-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 66158-30-3 | C9H11NO3 | 181.191 |
—— | 5-ethylthio-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid | 95797-12-9 | C8H9NO3S | 199.23 |
—— | 1-Methyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester | 15506-19-1 | C9H11NO3 | 181.191 |
—— | 2-hydroxynicotinic acid chloride | 28369-76-8 | C6H4ClNO2 | 157.556 |
—— | 1-butyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 64353-43-1 | C10H13NO3 | 195.218 |
—— | 1,2-dihydro-2-oxo-3,5-pyridinedicarboxylic acid, 3-t-butyl ester | 95797-08-3 | C11H13NO5 | 239.228 |
5-溴-2-羟基-烟酸 叔丁酯 | 5-bromo-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid, t-butyl ester | 95797-07-2 | C10H12BrNO3 | 274.114 |
—— | 1,2-dihydro-2-oxo-3,5-pyridinedicarboxylic acid, 3-t-butyl, 5-ethyl diester | 95797-10-7 | C13H17NO5 | 267.282 |
1,2-二氢-2-氧代-3-吡啶甲酰胺 | 2-hydroxynicotinamide | 10128-92-4 | C6H6N2O2 | 138.126 |
—— | 5-<(ethylamino)carbonyl>-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid | 95797-16-3 | C9H10N2O4 | 210.189 |
—— | 1,2-dihydro-2-oxo-5-phenylthio-3-pyridinecarboxylic acid | 95797-14-1 | C12H9NO3S | 247.274 |
3-(羟基甲基)-1-甲基-2(1h)-吡啶酮 | 3-(hydroxymethyl)-1-methylpyridin-2(1H)-one | 36721-61-6 | C7H9NO2 | 139.154 |
5-硝基-2-羟基吡啶-3-羧酸 | 2-hydroxy-5-nitronicotinic acid | 6854-07-5 | C6H4N2O5 | 184.108 |
1-苄基-2-氧代-1,2-二氢-3-吡啶羧酸 | 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 89960-36-1 | C13H11NO3 | 229.235 |
Scaffold hopping and structure-guided optimisation led to a new class of potent