有机化学 ›› 2014, Vol. 34 ›› Issue (7): 1458-1461.DOI: 10.6023/cjoc201401021 上一篇    下一篇

研究简报

桃小食心虫性信息素——(Z)-7-二十碳烯-11-酮的简便合成

杨晓梅a, 张玉顺b, 姚赟b, 陶云海b   

  1. a 云南中医学院中药学院 昆明 650500;
    b 云南大学化学科学与工程学院 昆明 650091
  • 收稿日期:2014-01-13 修回日期:2014-03-16 发布日期:2014-04-01
  • 通讯作者: 陶云海 E-mail:cloudsea2000@163.com
  • 基金资助:

    云南大学理(工)科校级科研(No.2011YB12)及云南省教育厅基金(No.2011Y112)资助项目.

Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth

Yang Xiaomeia, Zhang Yushunb, Yao Yunb, Tao Yunhaib   

  1. a School of Traditional Chinese Medicine, Yunnan University of Traditional Chinese Medicine, Kunming 650500;
    b School of Chemistry Science and Engineering, Yunnan University, Kunming 650091
  • Received:2014-01-13 Revised:2014-03-16 Published:2014-04-01
  • Supported by:

    Project supported by the Science and Technology Foundation of Yunnan University (No. 2011YB12) and the Foundation of Yunnan Province Department of Education (No. 2011Y112).

桃小食心虫是危害最大的果树害虫之一,其性信息素主要成分为(Z)-7-二十碳烯-11-酮. 从2,3-二氢呋喃出发,经酸水解得到4-羟基丁醛,与正庚基三苯基溴化磷制备的Wittig试剂反应得到(Z)-4-十一碳烯-1-醇,经氧化得到(Z)-4-十一碳烯醛,再经格氏加成得到(Z)-7-二十碳烯-11-醇,氧化后得到目标产物.

关键词: 桃小食心虫, Z)-7-二十碳烯-11-酮, 信息素合成, Wittig反应, 格氏加成

Peach fruit moth is one of the most serious pests, whose sex pheromone is (Z)-7-eicosen-11-one. Synthesis of the compound was achieved from 2,3-dihydrofuran. Firstly, acidic hydrolysis of 2,3-dihydrofuran gave 4-hydroxybutanal, which reacted with the ylide prepared from heptyltriphenylphosphonium bromide to afford (Z)-4-undecen-1-ol. The alcohol was oxidated followed by Grignard addition and further oxidation to give the target product.

Key words: carposina sasakii matsumura, (Z)-7-eicosen-11-one, pheromone synthesis, Wittig reaction, Grignard addition