刺激皮肤
6-羟基-1-萘甲酸被广泛用作有机合成中间体,并且是医药及染料生产的重要原料。近年来,酪氨酸激酶靶向药物(包括单抗和小分子化合物)在血液恶性肿瘤、肺癌、肾癌、结直肠癌、胃癌、肝癌等多种癌症中的开发与应用十分活跃。德立替尼是一种靶向VEGFR1、VEGFR2、FGFR1、PDGFRβ、c-Kit、c-Src的小分子多靶点酪氨酸激酶抑制剂,同类药物已成功应用于临床抗肿瘤治疗。
应用6-羟基-1-萘甲酸可作为有机合成中间体和医药中间体,在实验室研发过程及化工生产中广泛应用。
制备方法6-羟基-1-萘甲酸的制备步骤如下:在250ml四口瓶中,加入20g糠酸、19.3g苯甲醚和100ml氯苯,搅拌混合;油浴加热至内温35~40℃,缓慢加入55.9g无水三氯化铝。投料完毕后,在75-80℃下搅拌反应约24小时。随后降温,减压浓缩蒸出氯苯,并蒸馏完毕降至室温。接着向反应瓶中投入60ml N,N-二甲基甲酰胺并搅拌混合;常温下,缓慢、分次加入32.1g无水三氯化铝;投料完毕后,油浴加热至内温135℃,保温反应6小时。冷却至室温后,将反应液缓慢加至稀盐酸溶液中进行水解。用乙酸乙酯多次提取合并后,水洗并调节pH值至弱酸性。有机层减压浓缩回收乙酸乙酯,残留物用稀醇水脱色重结晶,最终获得灰色至淡黄色的粉末状6-羟基-1-萘甲酸,产率为43.5%,熔点为204.5~208.7℃,纯度达98.5%。
| 中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
|---|---|---|---|---|
| 6-甲氧基萘甲酸 | 6-methoxy-1-naphthoic acid | 36112-61-5 | C12H10O3 | 202.21 |
| 1-萘甲酸 | 1-naphthalenecarboxylic acid | 86-55-5 | C11H8O2 | 172.183 |
| 3-羟基-1,8-萘二甲酸酐 | 3-hydroxy-1,8-naphthalic acid anhydride | 23204-36-6 | C12H6O4 | 214.177 |
| —— | 6-sulfo-[1]naphthoic acid | 116692-16-1 | C11H8O5S | 252.248 |
| 中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
|---|---|---|---|---|
| 6-甲氧基萘甲酸 | 6-methoxy-1-naphthoic acid | 36112-61-5 | C12H10O3 | 202.21 |
| 6-羟基萘-1-甲酸甲酯 | methyl 6-hydroxy-1-naphthoate | 90162-13-3 | C12H10O3 | 202.21 |
| 6-乙氧基-1-萘甲酸 | 6-ethoxy-1-naphthoic acid | 731861-61-3 | C13H12O3 | 216.236 |
| 6-羟基-1-萘酸乙酯 | ethyl 6-hydroxy-1-naphthoate | 90162-14-4 | C13H12O3 | 216.236 |
| —— | 6-methoxy-1-naphthalenecarboxylic acid methyl ester | 61109-48-6 | C13H12O3 | 216.236 |
| —— | 6-(benzyloxy)-1-naphthoic acid | —— | C18H14O3 | 278.307 |
| —— | 6-acetoxy-1-naphthoic acid | 149066-23-9 | C13H10O4 | 230.22 |
| 6-羟基-1-萘甲醛 | 6-hydroxy-1-naphthaldehyde | 571206-45-6 | C11H8O2 | 172.183 |
| —— | 5-(hydroxymethyl)naphthalen-2-ol | —— | C11H10O2 | 174.199 |
| —— | 6-(pyridin-4-yloxy)-1-naphthoic acid | 1017969-39-9 | C16H11NO3 | 265.268 |
| —— | methyl 6-(pentyloxy)-1-naphthoate | 1353942-29-6 | C17H20O3 | 272.344 |
| 6-甲氧基-1-萘甲醛 | 6-methoxynaphthaldehyde | 3597-42-0 | C12H10O2 | 186.21 |
| —— | 6-cyano-1-naphthoic acid | 1975-47-9 | C12H7NO2 | 197.193 |
| —— | 5-Formyl-hydroxy-1-naphthoic Acid | —— | C12H8O4 | 216.193 |
| (6-甲氧基-1-萘基)甲醇 | 1-Hydroxymethyl-6-methoxynaphthalene | 61109-49-7 | C12H12O2 | 188.226 |
| —— | methyl 6-formyl-1-naphthoate | 1353942-14-9 | C13H10O3 | 214.221 |
| —— | 5-bromo-6-hydroxy-1-naphthoic acid | —— | C11H7BrO3 | 267.079 |
| 5-氟-6-羟基萘-1-羧酸 | 5-fluoro-6-hydroxy-1-naphthoic acid | 847802-85-1 | C11H7FO3 | 206.173 |
| 6-氰基-1-萘甲酸甲酯 | 6-Cyan-naphthoesaeure-(1)-methylester | 91804-22-7 | C13H9NO2 | 211.22 |
| 5-氟-6-羟基萘-1-羧酸甲酯 | methyl 5-fluoro-6-hydroxy-1-naphthoate | 388622-47-7 | C12H9FO3 | 220.2 |
| —— | methyl 6-((cis-4-methylcyclohexyl)oxy)-1-naphthoate | —— | C19H22O3 | 298.382 |
| —— | 6-(2-chloropyridin-4-yloxy)-1-naphthoic acid | 861880-86-6 | C16H10ClNO3 | 299.713 |
| 6-氨基-萘-1-羧酸甲酯 | methyl 6-amino-1-naphthoate | 91569-20-9 | C12H11NO2 | 201.225 |
| —— | 6-(pyrimidin-4-yloxy)-1-naphthoic acid | 1017969-41-3 | C15H10N2O3 | 266.256 |
| 1-(6-甲氧基-1-萘基)乙烷-1-酮 | 6-methoxy-1-acetylnaphthalene | 58149-89-6 | C13H12O2 | 200.237 |
| —— | 1-(6-Methoxy-1-naphthyl)-ethanol | 58149-98-7 | C13H14O2 | 202.253 |
| —— | (S)-1-(6-methoxy-1-naphthyl)ethanol | 179396-70-4 | C13H14O2 | 202.253 |
| —— | 4,6-dimethoxy-1,3,5-triazin-2-yl 6-hydroxy-1-naphthoate | 890130-29-7 | C16H13N3O5 | 327.296 |
| 5-溴-6-甲氧基萘-1-甲酸甲酯 | methyl 6-methoxy-5-bromo-1-naphthoate | 84532-70-7 | C13H11BrO3 | 295.133 |
| —— | methyl 6-((trans-4-(tert-butyl)cyclohexyl)oxy)-1-naphthoate | —— | C22H28O3 | 340.463 |
| —— | methyl 6-methoxy-5-chloro-1-naphthoate | 106852-08-8 | C13H11ClO3 | 250.682 |
| 6-羟基-N-甲基-1-萘羧酰胺 | 6-hydroxy-N-methyl-1-naphthalenecarboxamide | 847802-91-9 | C12H11NO2 | 201.225 |
| —— | 1-(6-ethoxynaphth-1-yl)ethanone | —— | C14H14O2 | 214.264 |
| —— | 6-trimethylsilanylethynyl-naphthalene-1-carboxylic acid methyl ester | 950643-03-5 | C17H18O2Si | 282.414 |
| —— | methyl 6-hexyl-1-naphthoate | 1353941-94-2 | C18H22O2 | 270.371 |
| —— | methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate | 255050-65-8 | C13H9F3O5S | 334.273 |
| —— | 6-carboxymethyl-naphthalene-1-carboxylic acid methyl ester | 950643-04-6 | C14H12O4 | 244.247 |
| —— | 6-chlorocarbonylmethyl-naphthalene-1-carboxylic acid methyl ester | 1245706-71-1 | C14H11ClO3 | 262.693 |
| —— | 5-ethylnaphthalen-2-ol | —— | C12H12O | 172.227 |
| —— | 6-(2-chloropyrimidin-4-yloxy)-1-naphthoic acid | 950643-29-5 | C15H9ClN2O3 | 300.701 |
| —— | 6-(2-amino-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid | 890129-77-8 | C15H11N3O3 | 281.271 |
| —— | 6-(6-chloropyrimidin-4-yloxy)-1-naphthoic acid | 890129-79-0 | C15H9ClN2O3 | 300.701 |
| —— | 1-(chloromethyl)-6-methoxynaphthalene | 861094-04-4 | C12H11ClO | 206.672 |
| —— | 6-(6-amino pyrimidin-4-yloxy)naphthalene-1-carboxylic acid | 890129-81-4 | C15H11N3O3 | 281.271 |
| 6-甲氧基-1-乙烯基萘 | 6-methoxy-1-vinyl-naphthalene | 74996-72-8 | C13H12O | 184.238 |
| (5-乙基-[2]萘基)-甲基醚 | 1-ethyl-6-methoxy-naphthalene | 91909-26-1 | C13H14O | 186.254 |
| —— | methyl 6-(1-hydroxyhexyl)-1-naphthoate | 1353942-15-0 | C18H22O3 | 286.371 |