有机化学 ›› 2016, Vol. 36 ›› Issue (3): 648-652.DOI: 10.6023/cjoc201508027 上一篇    下一篇

研究简报

异单叶大黄素及其类似结构茋类化合物的合成方法

赵剑阳a,b, 郑紫华a,b, 黄晴菲a, 邓金根c, 朱槿a, 王启卫a   

  1. a 中国科学院成都有机化学研究所 成都 610041;
    b 中国科学院大学 北京 100049;
    c 四川大学华西药学院 成都 610041
  • 收稿日期:2015-08-27 修回日期:2015-10-31 发布日期:2015-11-16
  • 通讯作者: 朱槿, 王启卫 E-mail:jinzhu@cioc.ac.cn;wqw@cioc.ac.cn
  • 基金资助:

    成都市高新区创新创业人才奖资助项目.

A Method for the Synthesis of the Isorhapontigenin and the Stilbene Compounds in Similar Structures

Zhao Jianyanga,b, Zheng Zihuaa,b, Huang Qingfeia, Deng Jingenc, Zhu Jina, Wang Qiweia   

  1. a Chengdu Institute of Organic Chemistry, Chinese Academy of Science, Chengdu 610041;
    b University of Chinese Academy of Sciences, Beijing 100049;
    c West China School of Pharmacy Sichuan University, Chengdu 610041
  • Received:2015-08-27 Revised:2015-10-31 Published:2015-11-16
  • Supported by:

    Project supported by the Award for Innovative Talents in Chengdu High-tech Zone.

发展了一种异单叶大黄素及其类似结构的茋类化合物的合成方法. 以3,5-二羟基苯甲酸为起始原料, 通过苄基保护酚羟基, Wittig-Horner反应构建反式二苯乙烯结构产物, 在钯碳/甲酸铵条件下, 以较高收率脱苄基得到异单叶大黄素, 总收率高达48%. 并将该催化体系成功地应用于一系列羟基茋类化合物的合成, 取得良好的效果. 各步反应收率高, 条件温和, 所用试剂成本低、毒性小, 操作简单、安全, 适合较大量生产. 为羟基茋类化合物的大批量合成提供了简便的途径.

关键词: 异单叶大黄素, 羟基茋类化合物, 钯碳/甲酸铵, 脱苄基

A method for the synthesis of the isorhapontigenin and the stilbene compounds in similar structures was developed. Using 3,5-dihydroxybenzoic acid as starting material, benzyl protecting the phenolic hydroxyl, via the Wittig-Horner reaction to construct the trans stilbene structure, and then debenzylation under the palladium on carbon/ammonium formate system condition, the isorhapontigenin could be obtained in the yield of up to 48%. The catalytic system was successfully applied in the synthesis of a series of hydroxyl stilbene compounds, which could achieve good results. All the reactions worked under mild conditions and obtained in good yield. Furthermore the materials were of cheap and less toxicity. It provided us a simple way to synthesize hydroxyl stilbene compounds in large scale.

Key words: isorhapontigenin, hydroxyl stilbene compounds, palladium on carbon/ammonium formate, debenzylation