| 由有机硼烷合成桃小食心虫性信息素 Z-7-二十烯-11-酮和 Z-7-十九烯-11-酮 |
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| 引用本文： | 卢奎,赵德杰,张国敏. 由有机硼烷合成桃小食心虫性信息素 Z-7-二十烯-11-酮和 Z-7-十九烯-11-酮[J]. 天然产物研究与开发, 1991, 0(1) |
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| 作者姓名： | 卢奎 赵德杰 张国敏 |
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| 作者单位： | 郑州粮食学院，武汉大学化学系，武汉大学化学系 武汉430072，武汉430072 |
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| 摘 要： | 研究了用有机硼烷的转化反应立体选择合成 Z-4-十一烯-1-醛(7)以及将其应用于桃小食心虫性信息素 Z-7-11-二十烯-11-酮(1)和 Z-7-十九烯-11-酮(2)的简便合成方法。用前文报告的经由有机硼烷一锅反应制备法获得的 Z-4-十一烯-1-醇(6),经氯铬酸吡啶(PCC)氧化生成 Z-4-十一烯-1-醛(7),后者与 Grignard 试剂作用,得中间物仲醇 Z-7-链烯-11-醇(8),然后使之氧化,即得预期的 Z-7-链烯-11-酮(1)和(2)。从起始原料1-已烯出发,总产率分别为36.9％和35.0％.
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| 关 键 词： | 立体选择合成 性信息素 有机硼烷 Z-7-链烯-11-酮 |
THE SYNTHESIS OF Z-7-EICOSN-11-ONE AND Z-7-NONADECEN-11-ONE THE SEX PHEROMONE OF PEACH FRUIT MOTH VIA ORGANOBORANES |
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| Lu Kui Zhao Bejie Zhang Guomin. THE SYNTHESIS OF Z-7-EICOSN-11-ONE AND Z-7-NONADECEN-11-ONE THE SEX PHEROMONE OF PEACH FRUIT MOTH VIA ORGANOBORANES[J]. Natural Product Research and Development, 1991, 0(1) |
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| Authors: | Lu Kui Zhao Bejie Zhang Guomin |
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| Abstract: | A simple and sterospecific synthesis of Z-4-undecen-1-al using the conversion of organoboranes and its application to the synthesis of z-7- eicosen-11-one (1) and Z-7-nonadecen-11-one (2),the sex pheromone of the peach fruit moth(Carposina niponensis Walsingham) has been inves- tigated.Z-4-undecen-1-ol (6),obtained via organoborane by a general and one pot preparation as described previously,redily reacts with pyri- dium chlorochromate (PCC) in methylene chloride at room temperature to produce the corresponding Z-4-undecen-1-al (7).The desired Z-7-alken-11 one (1) and (2) were synthesized by the oxidation of the intermediates Z-7-alken-11-ols (8),prepared from the reaction of (7) and Grignard reagents,with PCC in overall yield 36.9 and 35.0% respectively. |
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| Keywords: | Stereospecific synthesis Sex pheromones Orsanoboranes Z-7-alken-11-ones |
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