(1R,1aR,1bR,4S,5aS)-4-tert-Butyl-1-hydroxymethyl-1b-methyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one | 143890-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,1aR,1bR,4S,5aS)-4-tert-Butyl-1-hydroxymethyl-1b-methyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one
• 英文别名: (1R,2R,3R,4S,7S)-7-tert-butyl-3-(hydroxymethyl)-1-methyl-9-oxa-6-azatricyclo[4.3.0.02,4]nonan-5-one
• CAS: 143890-14-6
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: SVJVGWOCBKHWIQ-TURJHENQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,1aR,1bR,4S,5aS)-4-tert-Butyl-1-hydroxymethyl-1b-methyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one 在 四丁基碘化铵 、 sodium hydride 、 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 (1S,1aR,1bR,4S,5aS)-1-Benzyloxymethyl-4-tert-butyl-1b-methyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-ol
  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
• 作为产物：
  描述：

  (1R,1aS,1bR,4S,5aR)-4-tert-Butyl-1b-methyl-5-oxo-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以72%的产率得到(1R,1aR,1bR,4S,5aS)-4-tert-Butyl-1-hydroxymethyl-1b-methyl-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