(1R,5S)-3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one | 191222-61-4

• 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: (1R,5S)-3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one
• CAS: 191222-61-4
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: CQYKEEBVNYHASK-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,5S)-3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 (1R,5S)-3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexan-2-thione
  参考文献：
  名称：

  Stereochemistry and chiroptical spectra of 3-azabicyclo[3.1.0]hexan-2-ones and thiones

  摘要：

  Several optically active substituted 3-azabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues have been synthesized, and their circular dichroism spectra studied. The crystal structure of thiolactam 1a showed that the bicyclic skeleton of the title compounds assumes a sofa-like geometry. It is postulated that the cyclopropyl moiety and amide or thioamide group constitute an inherently chiral chromophore, helicity of which determines the Cotton effect sign corresponding to the n-pi* electronic transition. The weak pi-pi* Cotton effect of thiolactams shows opposite sign to that observed for the lowest energy excitation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00111-0
• 作为产物：
  描述：

  (1R,2S)-1-Phenyl-cyclopropane-1,2-dicarboxylic acid 1-methyl ester 在 sodium tetrahydroborate 、 草酰氯 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 苯 为溶剂， 生成 (1R,5S)-3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Stereochemistry and chiroptical spectra of 3-azabicyclo[3.1.0]hexan-2-ones and thiones

  摘要：

  Several optically active substituted 3-azabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues have been synthesized, and their circular dichroism spectra studied. The crystal structure of thiolactam 1a showed that the bicyclic skeleton of the title compounds assumes a sofa-like geometry. It is postulated that the cyclopropyl moiety and amide or thioamide group constitute an inherently chiral chromophore, helicity of which determines the Cotton effect sign corresponding to the n-pi* electronic transition. The weak pi-pi* Cotton effect of thiolactams shows opposite sign to that observed for the lowest energy excitation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00111-0

文献信息

• Stereochemistry and chiroptical spectra of 3-azabicyclo[3.1.0]hexan-2-ones and thiones
  作者：Maria J. Milewska、Maria Gdaniec、Tadeusz Poloński

  DOI：10.1016/s0957-4166(97)00111-0

  日期：1997.4

  Several optically active substituted 3-azabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues have been synthesized, and their circular dichroism spectra studied. The crystal structure of thiolactam 1a showed that the bicyclic skeleton of the title compounds assumes a sofa-like geometry. It is postulated that the cyclopropyl moiety and amide or thioamide group constitute an inherently chiral chromophore, helicity of which determines the Cotton effect sign corresponding to the n-pi* electronic transition. The weak pi-pi* Cotton effect of thiolactams shows opposite sign to that observed for the lowest energy excitation. (C) 1997 Elsevier Science Ltd.