异单叶大黄素及其类似结构茋类化合物的合成方法

引用本文: 赵剑阳, 郑紫华, 黄晴菲, 邓金根, 朱槿, 王启卫. 异单叶大黄素及其类似结构茋类化合物的合成方法[J]. 有机化学, 2016, 36(3): 648-652. doi: 10.6023/cjoc201508027 shu

Citation: Zhao Jianyang, Zheng Zihua, Huang Qingfei, Deng Jingen, Zhu Jin, Wang Qiwei. A Method for the Synthesis of the Isorhapontigenin and the Stilbene Compounds in Similar Structures[J]. Chinese Journal of Organic Chemistry, 2016, 36(3): 648-652. doi: 10.6023/cjoc201508027 shu

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;
2.
b 中国科学院大学北京 100049;
3.
c 四川大学华西药学院成都 610041

通讯作者: 朱槿, 王启卫; 朱槿, 王启卫

基金项目:
成都市高新区创新创业人才奖资助项目.

摘要: 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:

English

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

1.
a Chengdu Institute of Organic Chemistry, Chinese Academy of Science, Chengdu 610041;
2.
b University of Chinese Academy of Sciences, Beijing 100049;
3.
c West China School of Pharmacy Sichuan University, Chengdu 610041

Corresponding author: 朱槿, 王启卫; 朱槿, 王启卫

Received Date: 27 August 2015
Available Online: 16 November 2015
Fund Project:
成都市高新区创新创业人才奖资助项目.

Abstract: 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:

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异单叶大黄素及其类似结构茋类化合物的合成方法

通讯作者: 朱槿, 王启卫; 朱槿, 王启卫

English

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

Corresponding author: 朱槿, 王启卫; 朱槿, 王启卫

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

异单叶大黄素及其类似结构茋类化合物的合成方法

通讯作者: 朱槿, 王启卫; 朱槿, 王启卫

English

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

Corresponding author: 朱槿, 王启卫; 朱槿, 王启卫

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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