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有机化学
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有机化学 ›› 1999, Vol. 19 ›› Issue (5): 528-532. 上一篇    下一篇

研究论文

桃潜蛾性信息素的合成研究

黄锦霞;李焰;马兴泉;周忠强   

  1. 湖北大学化学与材料科学学院
  • 发布日期:1999-10-25

Study on synthesis of the sex pheromone of peach leafminer moth

Huang Jinxia;Li Yan;Ma Xingquan;Zhou Zhongqiang   

  • Published:1999-10-25

被引次数

7 | 1

(-)-莰烷磺内酰胺手性助剂与巴豆酸酰氯作用生成N-反式丁烯酰基衍生物(4),进而与n-C~4H~9MgBr进行Michael加成反应,发现在CuBr.Me~2S存在下,产物以S构型为主,且化学产率明显提高。经六步合成了桃潜蛾性信息素(S)-14-甲基-1-十八碳烯(1)及其对映异构体(R)-1。

关键词: 莰烷, 内酰胺P, 十八碳烯P, 磺酰胺P, 桃潜蛾, 性信息素, 不对称反应

Grignard agents (n-C~4H~9MgBr) in the presence of CuBr.Me~2S underwent 1, 4-Michael addition to N-crotonoyl-bornanesultam prepared from D-(-)-bornanesultam and crotonoic anhydride to give the main product of S-configuration. The sex pheromone of peach leafminer moth-(S)-14-methyl-1-octadecene 1 and its enantiomer (R)-1 were prepared via six steps of readions with the optical purity being 97% and 95%, respectively.

Key words: BORNANE, SULFAMIDE P, LACTAM P, SEX PHEROMONE

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