烟草甲性信息素及其异构体的简易合成法

Convenient synthesis of the sex pheromone and its isomers of Lasioderma serricorne

摘要: 从2,4-二甲基戊二酸出发,经酯化、还原、格氏反应、选择性保护分子中的一个羟基后,再经氧化及脱保护反应,以61%的总收率合成了烟草甲性信息素及其异构体——4,6-二甲基-7-羟基-3-壬酮(7); 7 经脱水环化反应,得到另一种烟草甲性信息素及其异构体——2,6-二乙基-3,5-二甲基-3,4-二氢呋喃(8)。各产物结构均经核磁共振氢谱、碳谱及质谱分析确证。

Abstract: The sex pheromone of Lasioderma serricorne and its isomer, 7-hydroxyl-4,6-dimethylnonan-3-one(7), have been synthesized in an overall yield of 61% starting from 2,4-dimethylglutaric acid via esterification, reduction, Grignard reaction, mono-etherification, oxidation and deprotection reaction sequence. Another sex pheromone and its isomer 2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran(8), were obtained by cyclodehydration of 7-hydroxy-4,6-dimethylnonan-3-one. The structures of products were confirmed by NMR and MS spectra spectroscopies.