对称二醇的选择性乙酰化及其在昆虫性信息素合成中的应用

Selective Acetylation of Symmetrical Diols and Its Application to the Synthesis of Sex Pheromones

α、ω-烷二醇的单保护衍生物是合成昆虫性信息素、前列腺素等天然产物的重要中间体。有关它的合成方法的研究,已引起了人们广泛的兴趣。1979年,James 等人首次报道了用连续抽提法进行对称二醇的选择性单酰化反应,并指出反应体系中水的用最是影响反应选择性的关键。然而,我们按文献[7]的配比多次重复,产率仅在50%左右,单酰化产物与双酰化产物之比小于10∶1。我们在文献[7]的基础上,采用经典的液-液提取法,用硫酸作催化剂。

The experimental results of selective monoacetylation of six kinds of Symmetricaldiol HO(CH_2)_nOH by liquid-liquid extraction in the presence of a strong acid catalyst werepresented.To illustrate the utility of this process,sex pheromones,(E,E)-9,11-tetrade-cadien-l-yl acetate was synthesized in three steps.