摘要
研究了白藜芦醇〔Resveratrol,(E)-3,4′,5-三羟基二苯乙烯〕的简便合成方法。以3,5-二甲氧基苯甲醛(Ⅰ)为起始原料,在无水三氯化铝的作用下经脱甲基反应得到3,5-二羟基苯甲醛(Ⅱ),然后与对羟基苯乙酸在乙酸酐和三乙胺的作用下发生Perkin缩合得到(E)-2-(4′-羟基苯基)-3-(3′,5′-二羟基苯基)丙烯酸(Ⅳ),最后经同步的脱羧-异构化反应得到目标化合物白藜芦醇(Ⅴ),总收率41.9%。在合成过程中,羟基无需保护和去保护、无需昂贵的脱甲基试剂,且脱羧和异构化一步完成,仅3步反应就成功合成了白藜芦醇。各中间体及产物结构经MS、IR及1HNMR确证。
A convenient method for the synthesis of resveratrol is described. 3,5-Dihydroxybenzaldehyde （Ⅱ） was obtained through demethylation of 3,5-dimethoxybenzaldehyde（Ⅰ） under anhydrous AlCl3, Perkin condensation between 3,5-dihydroxybenzaldehyde（Ⅱ） and 4-hydroxyphenyl acetic acid in the presence of acetic anhydride and triethylamine to obtain （E）-2-（4＇-hydroxyphenyl）-3-（3＇, 5＇- dihydroxyphenyl）-acrylic acid （Ⅳ）. Finally, a simultaneous decarboxylation/isomerization reaction of compound IV gives resveratrol in 41.9% overall yield. The protection of hydroxyl groups is unnecessary and expensive reagent isn＇t required in the demethylation process. Moreover, the decarboxylation/ isomerization was completed in one-pot reaction. The structure of the target compound and the key intermediates were verified by MS,IR and ^1HNMR.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2009年第6期580-584,共5页
Fine Chemicals
基金
广东省科技计划项目(2003B31603,2006B35604002)
广州市科技计划项目(2007J1-C0261)
2007年度中国科学院研究生科学与社会实践资助专项创新研究类项目~~
