有机化学 ›› 2019, Vol. 39 ›› Issue (9): 2650-2654.DOI: 10.6023/cjoc201906001 上一篇    下一篇

研究简报

8-羟基异香豆素的合成方法研究

郭冬冬a, 张武霞a, 王永强b   

  1. a 山西农业大学文理学院 山西太谷 030801;
    b 西北大学化学与材料科学学院 西安 710069
  • 收稿日期:2019-06-03 修回日期:2019-07-22 出版日期:2019-09-25 发布日期:2019-08-07
  • 通讯作者: 王永强 E-mail:wangyq@nwu.edu.cn
  • 基金资助:

    国家自然科学基金(No.31800678)、山西省优秀博士来晋工作奖励(No.SXYBKY201737)和山西农业大学科技创新基金(No.2017YJ38)资助项目.

Study on Synthetic Approach to 8-Hydroxyisocoumarin

Guo Dongdonga, Zhang Wuxiaa, Wang Yongqiangb   

  1. a College of Arts and Sciences, Shanxi Agricultural University, Taigu, Shanxi 030801;
    b Department of Chemistry & Materials Science, Northwest University, Xi'an 710069
  • Received:2019-06-03 Revised:2019-07-22 Online:2019-09-25 Published:2019-08-07
  • Contact: 10.6023/cjoc201906001 E-mail:wangyq@nwu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31800678), the Shanxi Excellent Doctor Grant Award (No. SXYBKY201737) and the Science and Technology Innovation Project of Shanxi Agricultural University (No. 2017YJ38).

对8-羟基异香豆素的合成方法进行研究.以麦氏酸为原料,通过傅克酰基化,羰基保护,酯基还原,脱保护,得到关键中间体3-乙炔基-2-(羟甲基)环己-2-烯-1-酮,再经酸性环化加成,环己烯酮环的芳构化,2,3-二氯-5,6-二氰对苯醌(DDQ)氧化等步骤,合成得到8-羟基异香豆素.合成的化合物结构经过1H NMR,13C NMR,IR,HRMS表征.

关键词: 异香豆素, 8-羟基异香豆素, 吡喃, 芳构化, 合成方法

A new method for the synthesis of 8-hydroxyisocoumarin is reported. 8-Hydroxyisocoumarin was synthesized from Meldrum's acid by Friedel-Crafts acylation, carbonyl protection, ester reduction and deprotection. The key intermediate 3-ethynyl-2-(hydroxymethyl)cyclohex-2-en-1-one was synthesized by acidic cycloaddition, aromatization of cyclohexanone ring and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) oxidation. The structures were characterized by 1H NMR, 13C NMR, IR, and HRMS.

Key words: isocoumarin, 8-hydroxyisocoumarin, pyran, aromatization, synthetic method