(1R*,2E,11S*)-2-(cyclohexylmethylene)-1-(phenylsilyl)methyloctahydropyrrolo[1,2-a]azepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: (1R*,2E,11S*)-2-(cyclohexylmethylene)-1-(phenylsilyl)methyloctahydropyrrolo[1,2-a]azepine
• 英文别名: [(1R,2Z,9aS)-2-(cyclohexylmethylidene)-1,3,5,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-1-yl]methyl-phenylsilane
• 化学式: C₂₃H₃₅NSi
• 分子量: 353.623
• InChiKey: HNDZZEOYOHHTRZ-AUAXGQTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯硅烷 、 1-(3-Cyclohexyl-prop-2-ynyl)-2-vinyl-azepane 在 (C₅Me₅)2YCH₃*THF 作用下， 以 环己烷 为溶剂， 反应 48.0h， 以82%的产率得到(1R*,2E,11S*)-2-(cyclohexylmethylene)-1-(phenylsilyl)methyloctahydropyrrolo[1,2-a]azepine
  参考文献：
  名称：

  Organolanthanide-Catalyzed Cyclization/Silylation of Nitrogen-Containing Enynes

  摘要：

  Cyclization/silylation reactions of nitrogen-containing enynes catalyzed by the complexes Cp*(2)-LnMe . THF (Ln = Y, Lu) were investigated. Utilizing standard conditions previously developed for carbocyclic systems, the Cp*2YMe . THF complex suffered from poor reactivity at room temperature with nitrogen alpha to the alkyne. This was overcome in the current studies either by slow catalyst addition or by using the smaller lutetium catalyst Cp*2LuMe . THF. The use of Cp*2LuMe . THF allowed the preparation of various nitrogen-containing ring systems in excellent yields with good to excellent diastereoselectivities at room temperature. The results of this study highlight the ability to tune the reactivity of an organolanthanide complex by changing the metal center.

  DOI：

  10.1021/jo9913311

文献信息

• Organolanthanide-Catalyzed Cyclization/Silylation of Nitrogen-Containing Enynes
  作者：Gary A. Molander、Christopher P. Corrette

  DOI：10.1021/jo9913311

  日期：1999.12.1

  Cyclization/silylation reactions of nitrogen-containing enynes catalyzed by the complexes Cp*(2)-LnMe . THF (Ln = Y, Lu) were investigated. Utilizing standard conditions previously developed for carbocyclic systems, the Cp*2YMe . THF complex suffered from poor reactivity at room temperature with nitrogen alpha to the alkyne. This was overcome in the current studies either by slow catalyst addition or by using the smaller lutetium catalyst Cp*2LuMe . THF. The use of Cp*2LuMe . THF allowed the preparation of various nitrogen-containing ring systems in excellent yields with good to excellent diastereoselectivities at room temperature. The results of this study highlight the ability to tune the reactivity of an organolanthanide complex by changing the metal center.