毛远湖,王丽丽,汤磊,刘浪,张吉泉.化学通报,2020,83(2):183-185. |
白藜芦醇的合成新方法 |
New Procedure for Synthesis of Resveratrol |
投稿时间:2019-04-24 修订日期:2019-11-15 |
DOI: |
中文关键词: 白藜芦醇 重氮化 Mizoroki-Heck偶联反应 合成 |
英文关键词:Resveratrol Diazotization Mizoroki-Heck coupling reaction Synthesis |
基金项目:贵州省化学合成药物研发利用工程技术研究中心平台项目(黔科合[2016]平台人才5402)、贵州省科技支撑项目(黔科合[2016]支撑2819)、贵州省大学生创新训练项目(2018520355)、贵阳市科技基金(筑科合[2017]30-28号)和贵州省科技基金重点项目(黔科合JZ字[2015]2001号)资助 |
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中文摘要: |
本文探索了合成白藜芦醇的新方法。以3,5-二甲氧基苯胺为原料,经重氮化、还原及乙酰化得到中间体N'-乙酰基-3,5-二甲氧基苯肼(4),中间体4与4-甲氧基苯乙烯经Mizoroki-Heck偶联反应得中间体5,脱去甲基即得到目标产物白藜芦醇,总收率约31.9%。中间体及目标产物的结构均经质谱及核磁氢谱确证。该路线操作简便、条件温和,可用于白藜芦醇的放大制备。 |
英文摘要: |
This study disclosed a new method for the synthesis of resveratrol. The key intermediate N'-(3,5-dimethoxyphenyl)acetohydrazide (4) was obtained by using 3,5-dimethoxyaniline as the starting material via diazotization, reduction and acetylation, which was condensed with 4-methoxystyrene to give the intermediate 5 via Mizoroki-Heck coupling reaction. The titled compound resveratrol (1) was prepared by final demethylation of 5 with a total yield of 31.9%. The structure of the intermediates and target product were confirmed by mass spectrum (MS) and 1H NMR. This procedure is characterized by handy operations and mild conditions, and can be used for the scale-up preparation of resveratrol. |
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