(1S,1aR,1bR,4S,5aS)-4-tert-Butyl-1b-methyl-1-vinyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one | 143890-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,1aR,1bR,4S,5aS)-4-tert-Butyl-1b-methyl-1-vinyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one
• 英文别名: (1R,2R,3S,4S,7S)-7-tert-butyl-3-ethenyl-1-methyl-9-oxa-6-azatricyclo[4.3.0.02,4]nonan-5-one
• CAS: 143890-09-9
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: GMHXXPLQAVOKGB-YNXVLUOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3S,7aR)-3-tert-butyl-7a-methyl-2,3-dihydropyrrolo[2,1-b][1,3]oxazol-5-one 、 vinyl diphenylsulfonium tetrafluoroborate 在 叔丁基锂 作用下， 生成 (1S,1aR,1bR,4S,5aS)-4-tert-Butyl-1b-methyl-1-vinyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one 、 (1R,1aR,1bR,4S,5aS)-4-tert-Butyl-1b-methyl-1-vinyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one
  参考文献：
  名称：

  An asymmetric route to enantiomerically pure 1,2,3-trisubstituted cyclopropanes

  摘要：

  Cycloaddition of various sulfur ylides to the chiral unsaturated lactams 1a, 1b led to cyclopropanated products containing a monosubstituted appendage. The stereochemical outcome is such that all the products are mainly (or exclusively) the kinetically controlled endo-syn-8, -9, or endo-anti-10. The latter occurs by virtue of an epimerization to the thermodynamically favored product. Removal of the chiral auxiliary following Wittig reaction on the intermediate carbinol amines (11, 15) gave chiral, nonracemic 1,2,3-trisubstituted cyclopropanes containing various functionalities (13, 16).

  DOI：

  10.1021/jo00049a038

文献信息

• An asymmetric route to enantiomerically pure 1,2,3-trisubstituted cyclopropanes
  作者：Daniel Romo、A. I. Meyers

  DOI：10.1021/jo00049a038

  日期：1992.11

  Cycloaddition of various sulfur ylides to the chiral unsaturated lactams 1a, 1b led to cyclopropanated products containing a monosubstituted appendage. The stereochemical outcome is such that all the products are mainly (or exclusively) the kinetically controlled endo-syn-8, -9, or endo-anti-10. The latter occurs by virtue of an epimerization to the thermodynamically favored product. Removal of the chiral auxiliary following Wittig reaction on the intermediate carbinol amines (11, 15) gave chiral, nonracemic 1,2,3-trisubstituted cyclopropanes containing various functionalities (13, 16).