桃条麦蛾性信息素5E-癸烯-1-醇及乙酸5E-癸烯酯的简便合成
收稿日期: 2016-08-18
修回日期: 2016-11-12
网络出版日期: 2017-01-10
基金资助
国家自然科学基金（Nos.21362018，81460525）及云南省应用基础研究计划（No.2014FB117）资助项目.
Simple Synthesis of 5E-Decen-1-ol and 5E-Decenyl Acetate, the Sex Pheromone of Peach Twig Borer
Received date: 2016-08-18
Revised date: 2016-11-12
Online published: 2017-01-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21362018, 81460525) and the Applied Basic Research Project of Yunnan Province (No. 2014FB117).
桃条麦蛾是危害果树的重要害虫之一，其性信息素主要成分为5E-癸烯-1-醇及乙酸5E-癸烯酯. 从丙烯醛出发，在钯催化下与乙炔加成得到5-溴-4E-戊烯醛，与甲氧基甲基三苯基氯化膦进行Wittig反应得到1E，5E/Z-1-溴-6-甲氧基己二烯，再与丁基溴化镁进行Kumada偶联反应得到1E/Z，5E-1-甲氧基癸二烯，水解得到5E-癸烯醛，再还原得到5E-癸烯-1-醇，最后酯化得到乙酸5E-癸烯酯.
关键词： 桃条麦蛾; 5E-癸烯-1-醇; 乙酸5E-癸烯酯; 信息素合成; Kumada偶联反应
黄飞 , 杨婉秋 , 张玉顺 , 姚赟 , 陶云海 . 桃条麦蛾性信息素5E-癸烯-1-醇及乙酸5E-癸烯酯的简便合成[J]. 有机化学, 2017 , 37(4) : 1046 -1050 . DOI: 10.6023/cjoc201608011
Peach twig borer is one of the most serious pests, whose sex pheromone is 5E-decen-1-ol and 5E-decenyl acetate. Synthesis of both compounds was achieved from acrolein. Firstly, a tandem addition reaction of acrolein with acetylene in the presence of Pd(OAc)2 gave 5-bromo-4E-pentenal, which reacted with the ylide prepared from (methoxymethyl)triphenyl- phodphonium chloride to afford (1E,5E/Z)-1-bromo-6-methoxyhexadiene. The compound was coupled with Grignard reagent, followed by hydrolysis and reduction to give 5E-decen-1-ol. Esterification of the alcohol afforded 5E-decenyl acetate.
[1] Bai, J.-W.; Zhao, J.-X.; Ma, W.-L. Sci. Silvae Sin. 1980, S1, 127 (in Chinese).
(白九维, 赵剑霞, 马文梁, 林业科学, 1980, S1, 127.)
[2] (a) Meng, X.-Z. Entomol. Knowl. 2000, 37, 75 (in Chinese).
(孟宪佐, 昆虫知识, 2000, 37, 75.)
(b) Meng, X.-Z. Chin. Bull. Entomol. 2007, 44, 477 (in Chinese).
(苏茂文, 张钟宁, 昆虫知识, 2007, 44, 477.)
[3] Ni, C.-C. World Pestic. 2008, 30, 31 (in Chinese).
(倪长春, 世界农药, 2008, 30, 31.)
[4] Roelofs, W. L.; Kochansky, J.; Anthon, E.; Rice, R.; Carde, R. Environ. Entomol. 1975, 4, 580.
[5] (a) Ohloff, G.; Vial, C.; Näf, F.; Pawlak, M. Helv. Chim. Acta 1977, 60, 1161.
(b) Odinokov, V. N.; Balezina, G. G.; Ishmuratov, G. Y.; Vakhitov, R. S.; Tolstikov, G. A. Chem. Nat. Compd. 1985, 21, 369.
(c) Poleschner, H.; Heydenreich, M.; Martin, D. Synthesis 1991, 1231.
(d) Doolittle, R. E.; Patrick, D. G.; Heath, R. H. J. Org. Chem. 1993, 58, 5063.
[6] (a) Buss, A. D.; Greeves, N.; Mason, R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1987, 2569.
(b) Levin, D.; Warren, S. Tetrahedron Lett. 1985, 26, 505.
(c) Buss, A. D.; Greeves, N.; Levin, D.; Wallace, P.; Warren, S. Tetrahedron Lett. 1984, 25, 357.
[7] Vig, O. P.; Sharma, M. L.; Gakhar, M.; Malik, N. Indian J. Chem., Sect. B 1980, 19, 755.
[8] Miyano, S.; Hokari, H.; Umeda, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 770.
[9] Chattopadhyay, A.; Mamdapur, V. R.; Chadha, M. S. Indian J. Chem., Sect. B 1983, 22, 1221.
[10] Zakharkin, L. I.; Petrushkina, E. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1985, 34, 193.
[11] Chauret, D. C.; Chong, J. M. Tetrahedron Lett. 1993, 34, 3695.
[12] Pederson, R. L.; Grubbs, R. H. US 20020022741, 2002 [Chem. Abstr. 2002, 143315].
[13] (a) Tao, Y.-H.; Cheng, W.-X.; Zhang, Y.-S.; Gu, K. Chem. J. Chin. Univ. 2005, 26, 1072 (in Chinese).
(陶云海, 程伟贤, 张玉顺, 古昆, 高等学校化学学校, 2005, 26, 1072.)
(b) Tao, Y.-H.; Cheng, W.-X.; Huang, X.-Z.; Zhang, Y.-S.; Gu, K. Chin. J. Org. Chem. 2005, 25, 558 (in Chinese).
(陶云海, 程伟贤, 黄相中, 张玉顺, 古昆, 有机化学, 2005, 25, 558.)
(c) Ma, Z.; Yang X.; Zhang, Y.; Huang, X.; Tao, Y. Synlett 2012, 23, 581.
(d) Tao, Y.; Yang, X.; Jin, Y.; Wang, Q. Synth. Commun. 2013, 43, 415.
(e) Yang, X.-M.; Zhang, Y.-Z.; Yao, Y.; Tao, Y.-H. Chin. J. Org. Chem. 2014, 34, 1458 (in Chinese).
(杨晓梅, 张玉顺, 姚赟, 陶云海, 有机化学, 2014, 34, 1458.)
[14] Wang, Z.; Lu, X.; Lei, A.; Zhang, Z. J. Org. Chem. 1998, 63, 3806.
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