有机化学 ›› 2001, Vol. 21 ›› Issue (6): 463-466. 上一篇    下一篇

研究论文

(R)-和(S)-石蚕蛾属于信息素的合成

李焰;黄锦霞;马兴泉;周忠强   

  1. 湖北大学化学与材料科学学院
  • 发布日期:2001-06-25

Synthesis of (R)-and (S)-enantiomers of the sex pheromone of caddisfly (hesperophylax occidentalis)

Li Yan;Huang Jinxia;Ma Xingquan;Zhou Zhongqiang   

  • Published:2001-06-25

以樟脑衍生物(-)-莰烷磺内酰胺为原料,经N-(E-2-烷烯酰基)莰烷-10,2-磺内酰胺与烷基格氏试剂的不对称Michael加成反应,LiAlH4还原断裂,3-甲基已醇的碘代反应及有机镉试剂与丙酰氯的偶联反应制得(R)-和(S)-石蚕蛾雄性性信息素6-甲基于-3-壬酮,其光学纯度达96%ee以上。

关键词: 樟脑, 莰烷磺内酰胺, 石蚕蛾, 性信息素, 甲基壬酮, 迈克尔加成反应

(R)-and (S)-6-methyl-3-nonanones, the sex pheromone produced by female caddisfly (Hesperophylax Occidentalis) were synthesized from R-camphor derivative-bornane-10,2-sultam via asymmetric Michael addition reaction of N-(E-2-enoyl) bornane-10,2-sultam with an alkyl magnesium reagent, reductive cleavage with LiAlH4, iodination of 3- methyl-1-hexanol and reaction of dialkyl cadmium with propionyl chloride. The enantiomeric excess of the total synthesis was over 96% ee.

Key words: CAMPHOR, SEX PHEROMONE, MICHAEL ADDITION REACTION

中图分类号: