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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (10): 1574-1579. 上一篇    下一篇

研究简报

氧化白藜芦醇的合成

孙洪宜1,2，肖春芬1,2，魏文1，陈煜1,2，吕泽良1,2,3，邹永*,1   

  1. (1中国科学院广州化学研究所 广州 510650)
    (2中国科学院研究生院 北京 100049)
    (3曲靖师范学院化学化工学院 曲靖 655011)
  • 收稿日期:2009-12-19 修回日期:2010-03-31 发布日期:2010-05-25
  • 通讯作者: 孙洪宜 E-mail:sunhy85@hotmail.com
  • 基金资助:

    广东省中国科学院战略合作;广州市科技计划

Synthesis of Oxyresveratrol

Sun Hongyi1,2 Xiao Chunfen1,2 Wei Wen1 Chen Yu1,2 Lü Zeliang1,2,3 Zou Yong*,1   

  1. (1 Guangzhou Institute of Chemistry, Chinese Academy of Science, Guangzhou 510650)
    (2 Graduate School of Chinese Academy of Sciences, Beijing 100049)
    (3 Department of Chemistry and Chemical Engineering, Qujing Normal University, Qujing 655011)
  • Received:2009-12-19 Revised:2010-03-31 Published:2010-05-25

PDF

2265

被引次数

11 | 4

研究了一种氧化白藜芦醇的简便合成方法. 以廉价易得的3,5-二羟基苯乙酮(1)为原料, 经甲基化及Willgerodt-Kindler重排反应得到3,5-二甲氧基苯乙酸(3), 3,5-二甲氧基苯乙酸(3)与2,4-二甲氧基苯甲醛(4)经Perkin反应构建二苯乙烯骨架, 再经脱羧及脱甲基异构化反应得到目标产物氧化白藜芦醇(7), 总收率为30%. 在合成过程中, 各步产物收率高、反应条件温和、操作简便, 各中间体及产物结构经MS, IR, 1H NMR及13C NMR确证.

关键词: 氧化白藜芦醇, 苯乙酸, Willgerodt-Kindler重排, 甲基化, Perkin反应, 脱羧反应, 脱甲基

A convenient method for the practical synthesis of oxyresveratrol is described. Starting from the readily available 3,5-dihydroxyacetophenone (1), 3,5-dimethoxyphenylacetic acid (3) can be achieved through methylation and Willgerodt-Kindler rearrangement. Perkin condensation between 3 and 2,4-dimethoxy- benzaldehyde (4) formed the stilbene skeleton, and by subsequent decarboxylation and demethylation/isomerization process, oxyresveratrol (7) was obtained in an overall yield of 30%. The synthetic method has several advantages such as mild reaction conditions, high yield of product and simple operations. The structures of the target compound and key intermediates were verified by MS, IR, 1H NMR and 13C NMR techniques.

Key words: oxyresveratrol, phenylacetic acid, Willgerodt-Kindler rearrangement, methylation, Perkin reaction, decarboxylation, demethylation