| 松毛虫性信息素(5Z,7E)-十二碳二烯醇的立体选择性合成 |
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| 引用本文： | 陶云海,程伟贤,张玉顺,古昆.松毛虫性信息素(5Z,7E)-十二碳二烯醇的立体选择性合成[J].高等学校化学学报,2005,26(6):1072-1075. |
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| 作者姓名： | 陶云海 程伟贤 张玉顺 古昆 |
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| 作者单位： | 1. 云南大学化学与材料工程学院;
2. 云南大学生物制药创新人才培养基地, 昆明650091 |
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| 摘 要： | 从简单原料乙炔出发,通过炔对丙烯醛的加成反应得到7-溴代-(4Z,6E)-庚二烯醛,再经乙二醇保护、Pd催化偶联、水解、Wittig反应和还原等步骤,立体选择性地得到松毛虫性信息素(5Z,7E)-十二碳二烯醇,其结构通过IR,NMR和MS等技术得到确认.
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| 关 键 词： | 松毛虫性信息素 (5Z 7E)-十二碳二烯醇 立体选择性合成 偶联反应 钯催化剂 |
| 文章编号： | 0251-0790(2005)06-1072-04 |
| 收稿时间： | 2004-06-12 |
Stereoselective Synthesis of(5Z,7E)-Dodecadien-1-ol |
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| TAO Yun-Hai,CHENG Wei-Xian,ZHANG Yu-Shun,GU Kun.Stereoselective Synthesis of(5Z,7E)-Dodecadien-1-ol[J].Chemical Research In Chinese Universities,2005,26(6):1072-1075. |
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| Authors: | TAO Yun-Hai CHENG Wei-Xian ZHANG Yu-Shun GU Kun |
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| Institution: | 1. School of Chemistry and Material Engineering;
2. Biomedical Research and Training Center, Yunnan University, Kunming 650091, China |
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| Abstract: | Sexpheromone of Dendrolimus Spp. is composed of (5Z, 7E)-5,7-Dodecadien-1-ol(1) and its acetate and propionate. At first 7-bromo-(4Z, 6E)-heptadien-1-al(2) was stereoselectively synthesized by the tandem addition reaction of acrolein with acetylene in the presence of Pd(OAc)_2. Novel stereoselective synthesis of (5Z, 7E)-5,7-Dodecadien-1-ol was achieved in five steps, using palladium-catalyzed coupling reaction of 7-bromo-(4Z, 6E)-4,6-heptadiene-1-al ethylene acetal from production of the above aldehyde with Grignard reagent as the key step. The structures of all the compounds were confirmed by IR, NMR and MS spectra. |
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| Keywords: | Dendrolimus Spp (5Z 7E)-Dodecadien-1-ol Stereoselective synthesis Coupling-reaction Palladium catalyst |
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