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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (9): 1466-1469. 上一篇    下一篇

研究简报

β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯/冰片酯合成研究

张群正*,a,b 董 岩a 南叶飞c 蔡雪刁a 郑晓晖c   

  1. (a西安石油大学化学化工学院 西安 710065)
    (b陕西科技大学资源与环境学院 西安 710021)
    (c西北大学西部资源生物与现代生物技术省部共建教育部重点实验室 西安 710069)
  • 收稿日期:2008-09-02 修回日期:2009-03-10 发布日期:2009-12-30
  • 通讯作者: 张群正

Synthesis of β-(3,4-Dihydroxyphenyl)-α-hydroxy Propionic Acid Esters

Zhang, Qunzheng *,a,b Dong, Yan a Nan, Yefei c Cai, Xuediao a Zheng, Xiaohui c   

  1. (a College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065)
    (b College of Resource and Environment, Shaanxi University of Science & Technology, Xi’an 710021)
    (c Key Laboratory of Resource Biology & Morden Biotechnoloby in Western China, Ministry of Education,
    Nortwest University, Xi’an 710069)
  • Received:2008-09-02 Revised:2009-03-10 Published:2009-12-30
  • Contact: Zhang, Qunzheng

PDF

2122

被引次数

37

以3,4-二羟基苯甲醛为起始原料, 经苄基保护、Darzens环氧化、Lewis酸开环、NaBH4还原、催化加氢脱保护得到β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯和β-(3,4-二羟基苯基)-α-羟基丙酸冰片酯, 所得化合物的结构通过1H NMR、13C NMR, IR, MS证实. 该方法操作简单、毒性低、产物易于纯化.

关键词: 酯化, β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯, β-(3,4-二羟基苯基)-α-羟基丙酸冰片酯, 超强酸催化

β-(3,4-Dihydroxyphenyl)-α-hydroxy propionic acid isopropyl and propionic acid borneol esters have been synthesized by taking 3,4-dihydroxybenzaldehyde as a raw material, through its benzyl protection, darzens ring-oxidation, Lewis acid ring-opening, NaBH4 reduction, deprotection of the Bzl groups by catalytic hydropyrolysis. The structures of products have been characterized by the 1H NMR, 13C NMR, IR and MS techniques. The method contains the merits of easy manipulation and low toxcity.

Key words: β-(3,4-dihydroxyphenyl)-α-hydroxy propionic acid isopropyl ester, β-(3,4-dihydroxylphenyl)-α-hydroxy propionic acid borneol ester, super acid catalysis, esterification