6-methyl-5-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-methyl-5-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
• 英文别名: (1S,5R,6R)-6-methyl-5-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: FAKRRGQKEVVNAG-HLUHBDAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 1-phenyl-2-(trimethylsilyl)cycloprop-2-ene-1-carboxylate 在 甲醇 、 二异丁基氢化铝 、 potassium carbonate 、 N-甲基-L-脯氨醇 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 30.0h， 生成 6-methyl-5-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Enantioselective, Facially Selective Carbomagnesation of Cyclopropenes

  摘要：

  Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step.

  DOI：

  10.1021/ja058101q