高等学校化学学报

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用蒜头果油脂合成大环内酯的新方法

刘雄民, 李伟光, 李飘英, 周永红   

  1. 广西大学化学化工学院, 南宁530004
  • 收稿日期:2006-06-15 修回日期:1900-01-01 出版日期:2007-05-10 发布日期:2007-05-10
  • 通讯作者: 刘雄民

A New Method for Synthesis of Mcrocyclic Lactones via Malania Olceifera Chum Oil

LIU Xiong-Min*, LI Wei-Guang, LI Piao-Ying, ZHOU Yong-Hong   

  1. School of Chemistry & Chemical Engineering, Guangxi University, Nanning 530004, China
  • Received:2006-06-15 Revised:1900-01-01 Online:2007-05-10 Published:2007-05-10
  • Contact: LIU Xiong-Min

摘要: 通过蒜头果油臭氧化、还原制备ω-羟基脂肪酸三甘油酯, 然后在催化剂作用下关环合成大环内酯. 该方法不需要皂化和酸化反应, 也不需要分离出二十四碳-15-烯酸, 缩短了蒜头果油合成环十五内酯的步骤, 为通过油脂合成大环内酯提供了简单合成方法.

关键词: 蒜头果油, 环十五内酯, 臭氧化, 大环内酯

Abstract: Synthesis of mcrocyclic lactones has been applied to medical and flavor field. Triglycerides(2) of ω-hydroxycarboxylic acids synthesized from malania oleifera chum oil(1) via ozonization and reduction, and compound 2 were catalytically transformed to macrocyctic lactones(3). This is a new method involving fewer steps and a 61% yield of cyclopentadecanolide was obtained. The reactive properties of macrolactonization of ω-hydroxycarboxylic acids were also studied. The result obtained shows that the priority order of macrolactonization as follows: 11-undecalactone>cyclotridecanolide>cyclopentadecanolide, i.e. the short chain ω-hydroxycarboxylic acids were preferentially cyclized.

Key words: Malania olceifera chum oil, Cyclopentadecanolide, Ozonization, Macrocyclic lactone

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