姜黄素与丙酸酐不对称反应产物的合成  

Study on Asymmetric Reaction of Curcumin and Propionic Anhydride

作　　者：秦伟[1] 王鑫[1] 刘磊[1] 庞磊[2] 王静[1] 

机构地区：[1]齐齐哈尔医学院药学院,黑龙江齐齐哈尔161000 [2]齐齐哈尔医学院附属第三医院,黑龙江齐齐哈尔161000

出　　处：《中国药房》2014年第11期984-986,共3页China Pharmacy

基　　金：黑龙江省教育厅科学技术研究(面上)项目(No.12531821)

摘　　要：目的:合成姜黄素与丙酸酐的不对称反应产物——1-(4-丙酰氧基-3-甲氧基苯基)-7-(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮(化合物1)。方法:以姜黄素和丙酸酐为原料,吡啶为催化剂,二氯甲烷/N,N-二甲基甲酰胺(DMF)为溶剂,进行不对称反应,经柱层析分离纯化,得目标化合物1,并进行核磁共振结构表征,以收率为指标,确定最佳反应条件(投料比、温度、时间、吡啶用量)。结果:制备得到了化合物1(收率:81.2%,纯度:99.0%),并经结构表征证实。化合物1的最佳反应条件是姜黄素与丙酸酐比为1∶1.5(m/m),反应温度为30Ⅸ,时间为30 min,吡啶用量为0.5%。结论:以确定的反应条件可得到目标化合物1。该工艺操作简便,收率和纯度高,可为姜黄素结构修饰的进一步研究提供参考。OBJECTIVE： To asymmetric synthesize the 1-（4-propionyloxy-3-methoxyphenyl）-7-（4-hydroxy-3-methoxyphe- nyl）-1,6-heptadiene-3, 5-dione （compound 1） of curcumin and propionic anhydride.METHODS： Compound 1 was synthesized by using curcumin and propionic anhydride as raw material, pyridine as catalytic agent, dichloromethane/N, N-dimethylformamide （DMF） as solvent; the structure of it was characterized by NMR. The optimal reaction condition such as temperature, time and amount of pyridine were well studied with yield as index. RESULTS：Compound 1 （yield of 81.2 %, purity of 99.0 % ） was obtained and confirmed. The optimal reaction of compound 1 was as follows： curcumin and propionic anhydride ratio of 1：1.5（m/m）, reac- tion temperature of 30℃, reaction time of 30 min, pyridine amount of 0.5%. CONCLUSIONS： Target compound 1 could be ob- tained by this technology. It is easy and simple to handle with high yield and high purity. And it can be used as reference for further study on the structure modification of curcumin.

关 键 词：姜黄素 不对称反应 丙酸酐 

分 类 号：R285[医药卫生—中药学] Q426[医药卫生—中医学]