光学活性桃潜叶蛾性信息素的合成

Synthesis of Chiral Peach Leafminer Moth's Sex Pheromone

探讨了桃潜叶蛾的危害和防治措施,对桃潜叶蛾性信息素的有效成分14-甲基-1-十八碳烯的合成进行了考察。以2-甲基己酸、1,9-二溴壬烷、烯丙基氯等为原料,利用格氏偶联反应,合成了外消旋14-甲基-1-十八碳烯,全程产率38%。以奎宁拆分2-甲基己酸得到的(S)-2-甲基己酸为原料,经过相同的反应步骤合成了(S)-14-甲基-1-十八碳烯,全程产率31%。实验表明,20min的溴代烷/四氢呋喃溶液的滴加时间以及n(Li2CuCl4)/n(格氏试剂)=3%即可保证较高的反应收率。所得产品的结构经IR、MS和1H NMR进行了表征。

The synthesis of peach leafminer moth＇s sex pheromone was carried out in this paper. The racemic 14-methyl-l-octadecene was prepared by the Grignard coupling reaction from the starting materials 2-methyl hexanoic acid, 1,9-dibromononane and allyl chloride. The overall yield is 38%. The （S）-14-methyl-l-octadecene was also prepared by the same methods from the （S）-2-methyl hexanoic acid obtained from the resolution of 2-methyl hexanoic acid with quinine. The overall yield is 31%. The 20 rains adding time of alkyl bromide/THF solution and the 3% molar ratio of Li2CuC14/Grignard reagent are efficient for the good yield of the target compound. The structure of the compound was characterized by IR, MS and 1HNMR.