| 梨小食心虫性信息素的新法合成 |
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| 引用本文： | 刘复初,李雁武,林军,朱洪友,李全,宗乾收.梨小食心虫性信息素的新法合成[J].高等学校化学学报,2003,24(6):1040-1042. |
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| 作者姓名： | 刘复初 李雁武 林军 朱洪友 李全 宗乾收 |
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| 作者单位： | 云南大学应用化学系, 昆明 650091 |
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| 摘 要： | 梨小食心虫 (Grapholia molesta)是一种世界性果树害虫 ,主要危害梨、桃和苹果等果树 . 1 96 5年Geroge等 1] 从该雌蛾腹部分离得到其性信息素 . 1 96 9年 Roelofs等 2 ] 鉴定其结构为 8(Z/E) -十二碳烯 - 1 -醇乙酸酯 (6 ) .国内外对其生物活性进行了大面积田间试验 ,并用于
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| 关 键 词： | 性信息素 油酸 硼氢化反应 臭氧化 Wittig反应 |
| 文章编号： | 0251-0790(2003)06-1040-03 |
| 收稿时间： | 2002-05-21 |
A New Route for the Synthesis of Grapholitha Molesta Sex Pheromone |
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| LIU Fu-Chu ,LI Yan-Wu,LIN Jun,ZHU Hong-You,LI Quan,ZONG Qian-Shou.A New Route for the Synthesis of Grapholitha Molesta Sex Pheromone[J].Chemical Research In Chinese Universities,2003,24(6):1040-1042. |
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| Authors: | LIU Fu-Chu LI Yan-Wu LIN Jun ZHU Hong-You LI Quan ZONG Qian-Shou |
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| Institution: | Department of Applied Chemistry, Yunnan University, Kunming 650091, China |
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| Abstract: | The sex pheromone of grapholitha molesta 8(Z/E)-dodecen-1-ol acetate (6) was synthesized bYUsing oleic acids as the raw material. 1,8(Z)-Heptadecadiene (2) was obtained from the decarbonylation reaction of oleic acid (1) in the presence of palladium complexes catalyst. Selective hydroboration and oxidation of 2 by Ca(BH422O2 system gave 8(Z)-heptadecen-1-ol (3), which then was acetylized by treatment with Ac 2O/pyridine to afford 8(Z)-heptadecen-ol acetate(4). The compound 4 was ozonized to form the keYINtermediate 8-acetoxyoctanal (5), then compound 5 was coupled with the Wittig regents to obtain the title compound 8(Z/E)dodecen-1-ol acetate (6), Z/E molar ratio is 25;75. The overall yield was 45%. The structures of all the compounds were confirmed by IR, MS and NMR spectra. |
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| Keywords: | Sex pheromone Oleic acid Hydroboration Ozonization Wittig reaction |
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