9,10-二羟基环十六内酯的合成  

Synthesis of 9,10-Dihydroxycyclohexadecanolide

作　　者：高山[1,2] 刘兰香[1] 张弘[1] 孙彦琳[2] 周梅村[2] 郑华[1] 

机构地区：[1]中国林业科学研究院资源昆虫研究所,云南昆明650224 [2]昆明理工大学化学工程学院,云南昆明650500

出　　处：《化学世界》2016年第4期213-216,220,共5页Chemical World

基　　金：国家林业公益性行业科研项目(201204602)

摘　　要：紫胶桐酸是一种具有生物活性的长链羟基烷酸,可用于大环内酯的合成。以紫胶桐酸多羟基作为起始原料,利用高度稀释的合成策略,通过缩醛选择性保护邻二醇、直链前体内酯化环合及酸催化环缩醛脱保护三步反应制备得到了目标产物9,10-二羟基-环十六内酯,总收率为31%,所得产物经红外光谱(IR)、核磁共振氢谱和碳谱(1 H NMR和13C NMR)、电喷雾质谱(ESI-MS)表征得以证实。实验均在室温下进行,反应条件温和,简洁有效。Aleuritic acid is one of chain hydroxycarboxylic acids which can be used for the synthesis of large ring lactone.Based on its structural hydroxyl groups,9,10-dihydroxycyclohexadecanolide was synthesized from aleuritic acid by three reaction steps.Firstly,the vicinal diol groups was protected through selective acetal reaction.Then the middle product was esterified by 2-methyl-6-nitrobenzoic anhydride and 4-dimethylaminopyridine.Finally,the target product was obtained through catalyzed deprotection.The total yield was 31%.The chemical structure of the synthesized intermediates and product was identified by IR,1 H NMR,13 C NMR and ESI-MS.The reaction conditions for the whole experiment were mild,simple and effective.

关 键 词：紫胶桐酸 大环内酯 酯化 高度稀释 

分 类 号：TQ655[化学工程—精细化工]