白皮杉醇的合成研究

Synthesis of Piceatannol

摘要:

以3,4-二甲氧基苄醇为原料，通过溴代、Arbuzov重排反应、Wittig-Horner反应和脱甲基化反应得到目标产物（E）-3,3′，4,5′-四羟基二苯乙烯，即白皮杉醇。本文从溴代试剂、Arbuzov重排反应温度、Wittig-Horner反应中溶剂及脱甲基反应试剂等各种因素考察了对产物产率的影响，实验最佳条件为：以三溴化磷为溴代试剂，Arbuzov重排反应条件为100℃反应1h, 120～130℃反应3～4h，以DMF为Wittig-Horner反应溶剂，无水ACl3作为脱甲基化试剂。通过IR、1H NMR及13C NMR确定了目标产物的结构。

Abstract:

Starting from the 3, 4-dimethoxybenzyl alcohol, 3, 3′, 4, 5′-tetrahydroxystilbene (piceatannol) was synthesized through bromation, Arbuzov Rearrangement followed by Wittig-Horner reaction and demethylation reaction. The effects of brominating agents, the temperature of Arbuzov Rearrangement, solvent in Wittig-Horner reaction, and demethylation agents were investigated .The optimal conditions were: phosphorus tribromide as the brominating agent, Arbuzov Rearrangement conditions of 100 ℃ for 1h and then 120 ~ 130 ℃for 3 ~ 4h, dimethylformamide as the solvent in Wittig-Horner reaction , dry aluminum chloride as the demethylation agent. The structure of the target molecules was confirmed by using IR、1H and 13C NMR spectra.