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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (5): 763-768. 上一篇    下一篇

研究论文

(2R)-莰烷磺内酰法合成红褐林蚁和多点林蚁哟虫信息 素的主要组分3-乙基－4 －甲基戊酸甲酯

杨焰;谌了容;黄锦霞;任君;周忠强   

  1. 湖北大学化学与材料科学学院;武汉大学分析测试中心.武汉(430072)
  • 发布日期:2001-05-15

Synthesis of a major component of the pheromones of formica rufa and formica polyctena methyl -3-ethyl -4- methylpentanoate using 2R-- bornane ----10, 2--sultam as chiral auziliary

Yang Yan;Chen Lerong;Huang Jinxia;Ren Jun;Zhou Zhongqiang   

  1. Wuhan Univ., Center of Anal Measur.Wuhan(430072)
  • Published:2001-05-15

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以(2R)-莰烷磺内酰胺为手性助剂，经不对称Michale加成、断裂等简单步骤合成红褐林蚁和多点林蚊尾虫信息(3R)和(3S)-3-乙基－4－甲基戊酸甲酯(1)，该合成的对映异构体纯度均达94％e.e.以上，另外其关于中间体(3'R)－N'－3'-乙基-4-甲基戊酰基莰烷-10,2-磺内酰胺的单晶结构进行了报道，并讨论了在有或无CuBr·Me~2时Michael加成反应的机理。

关键词: 莰烷磺内酰胺, 迈克尔加成反应, 昆虫信息素, 反应机理, 红褐林蚁, 多点林蚁, 乙基甲基戊酸甲酯

(R) and (S) --methyl --3----ethyl--4--- methylpentanoate, one of the main components of pheromones of the red wood at (formica rufa ) and the small forest ant (formica polyctena ). was synthesized with asymmetric Michael addition as key step. The enantiomeric excess of the target products is over 94%. The X--ray crystallographic data of a key immediate, N-[(3R)-3---ethyl --4----4methyl valeryl]--(--) -- bornane ---10,2 ---sultam, is also reported. The mechanism of the Michael addirion in the presence or absence of CuBr·Me~2S remains unknwn.

Key words: MICHAEL ADDITION REACTION, REACTION MECHANISM

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