13-cis-维A酰衍生物合成方法的改进  

Improvement on the Synthesis of 13-cis-Retinoic Acid Derivatives

作　　者：易卫国[1] 刘志常[1] 向莉[1] 刘西洋[1] 陈静[1] 向建南[1] 

机构地区：[1]湖南大学化学化工学院

出　　处：《应用化学》2007年第5期521-524,共4页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金(20472018);湖南省自然科学基金(03JJY3016)资助项目

摘　　要：改进并建立了以4-二甲氨基吡啶(DMAP)-对甲苯磺酸盐为催化剂,二环己基碳酰亚胺(DCC)为缩合剂直接用13-cis-维A酸与醇、酚或胺合成13-cis-维A酰衍生物的方法。合成了8种新目标化合物,收率80%～95%,核磁共振氢谱和碳谱研究表明,13-cis-维A酰部分的构型均保持不变。合成方法彻底抑制了反应中N-异维A酰基脲的副反应,而且反应条件温和,对于极易异构化的13c-is-维A酸的酯化和酰胺化反应十分有利。To improve the synthetic method of 13-cis-retinoic acid derivatives, the title compounds were synthesized directly from 13-cis-retinoic acid and alcohols, phenols or amines with DCC as the condensation reagent under the catalysis of 4-（dimethylamino）pyridinium p-toluenesulfonate prepared in our lab. Eight new compounds were obtained in 80% -95% yields and in a high isomeric purity, which were characterized by NMR. The side reaction that converts 13-cis-retinoic acid to unreactive N-retinoylurea was completely suppressed. The reaction proceeds under mild conditions and is favorable to the esterification and amidation of thermally-, chemically- and ultraviolet-sensitive 13-cis-retinoic acid and its analogues.

关 键 词：药物化学 方法改进 异维A酰化 cis-维A酸衍生物 二环己基碳酰亚胺 

分 类 号：O626[理学—有机化学]