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2024 , Vol. 44 >Issue 1: 301 - 308

DOI: https://doi.org/10.6023/cjoc202305023

研究论文

黑腹尼虎天牛接触性信息素的不对称合成

  • 于士航 ,
  • 刘嘉威 ,
  • 安碧玉 ,
  • 边庆花 ,
  • 王敏 ,
  • 钟江春
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  • 中国农业大学理学院 应用化学系 北京 100193
†共同第一作者.

收稿日期: 2023-05-17

  修回日期: 2023-06-24

  网络出版日期: 2023-07-20

基金资助

国家重点研发计划(2017YFD0201404)

收起

Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius)

  • Shihang Yu ,
  • Jiawei Liu ,
  • Biyu An ,
  • Qinghua Bian ,
  • Min Wang ,
  • Jiangchun Zhong
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  • Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
†These authors contributed equally to this work.
*E-mail: ;
E-mail:

Received date: 2023-05-17

  Revised date: 2023-06-24

  Online published: 2023-07-20

Supported by

National Key Research and Development Program of China(2017YFD0201404)

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摘要

黑腹尼虎天牛是一种危害林木与果树的蛀干害虫, 其接触性信息素为(R)-9-甲基二十七烷、(R)-7-甲基二十五烷和(R)-7-甲基二十七烷. 以(S)-环氧丙烷为手性源, 环氧丙烷与格氏试剂的开环加成、仲磺酸酯与格氏试剂的SN2烷基化以及手性醛的Wittig偶联为关键步骤, 发展了一种新的合成黑腹尼虎天牛接触性信息素的方法.

关键词： 黑腹尼虎天牛; 接触性信息素; 手性源; (S)-环氧丙烷; 不对称合成

本文引用格式

于士航 , 刘嘉威 , 安碧玉 , 边庆花 , 王敏 , 钟江春 . 黑腹尼虎天牛接触性信息素的不对称合成[J]. 有机化学, 2024 , 44(1) : 301 -308 . DOI: 10.6023/cjoc202305023

Abstract

Neoclytus acuminatus acuminatus (Fabricius) is a wood-boring pest of forests and orchards. Its contact sex pheromones were (R)-9-methylheptacosane, (R)-7-methylheptacosane and (R)-7-methylpentacosane. A new and efficient synthesis of the contact sex pheromone was developed from chiral synthon of (S)-2-methyloxirane. This procedure mainly involved ring-opening reaction of (S)-2-methyloxirane, SN2 allylation of secondary tosylate and Wittig coupling of chiral aldehyde.

Key words： Neoclytus acuminatus acuminatus; contact sex pheromone; chiral source; (S)-2-methyloxirane; asymmetric synthesis

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