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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (12): 2126-2130. 上一篇    下一篇

研究简报

小菜蛾性信息素的合成

宗广辉，颜世强，梁晓梅，王道全，张建军*   

  1. (中国农业大学理学院 农业部农药化学与应用技术重点开放实验室 北京 100193)
  • 收稿日期:2011-04-02 修回日期:2011-06-17 发布日期:2011-07-21
  • 通讯作者: 张建军 E-mail:zhangjianjun@cau.edu.cn

Synthesis of the Sex Pheromone of Plutella xylostella (L.)

ZONG Guang-Hui, YAN Shi-Qiang, LIANG Xiao-Mei, WANG Dao-Quan, ZHANG Jian-Jun   

  1. (Key Laboratory of Pesticide Chemistry and Application Technology, College of Science, China Agricul-tural University, Beijing 100193)
  • Received:2011-04-02 Revised:2011-06-17 Published:2011-07-21
  • Contact: Zhang Jian-Jun E-mail:zhangjianjun@cau.edu.cn

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被引次数

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以十一碳烯醇和碘戊烷为原料, 经过苯甲酰基保护、9-硼双环[3.3.1]-壬烷(9-BBN)硼氢化后氧化、氯铬酸吡啶盐(PCC)氧化、Wittig反应、脱苯甲酰基五步反应得到顺-11-十六碳烯-1-醇(Z11-16:OH), 五步反应总收率53%. 顺-11-十六碳烯-1-醇经PCC氧化或Ac2O乙酰化分别得到顺-11-十六碳烯-1-醛(Z11-16:Ald)、顺-11-十六碳烯-1-醇乙酸酯(Z11-16:Ac), 目标化合物及主要中间体结构经NMR, IR和MS确证. 合成方法路线短, 操作简便, 收率较文献中的方法有较大提高.

关键词: 小菜蛾, 性信息素, 合成, Wittig反应

The main components of the sex pheromone of Plutella xylostella (L.) were synthesized from 10-undecen-1-ol and iodopentane as starting materials. Firstly, Z11-16:OH was obtained by benzoylation of 10-undecen-1-ol, then hydroboration with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by oxidation, further oxidation with pyridinium chlorochromate (PCC), and then by Wittig reaction and debenzoylation in a total yield of 53% for 5 steps. Z11-16:Ald and Z11-16:Ac were prepared from Z11-16:OH by oxidation or acetylation. Their structures were confirmed by NMR, IR and MS techniques. This is a good method with the advantages of short synthetic routes, normal operation and higher yield as compared with the reported methods.

Key words: Plutella xylostella (L.), sex pheromone, synthesis, Wittig reaction