(1R,2S)-2-(1-methylethoxycarbonyl)-1-phenyl-1-cyclopropanecarboxylic acid | 185683-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-2-(1-methylethoxycarbonyl)-1-phenyl-1-cyclopropanecarboxylic acid
• 英文别名: (1R,2S)-1-phenyl-2-propan-2-yloxycarbonylcyclopropane-1-carboxylic acid
• CAS: 185683-70-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: WRBNZKUSJIEMJU-RISCZKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(1-methylethoxycarbonyl)-1-phenyl-1-cyclopropanecarboxylic acid 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 (1S,5S)-3-methyl-5-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
• 作为产物：
  描述：

  异丙醇 、 (1R,5S)-1-Phenyl-3-oxa-bicyclo[3.1.0]hexane-2,4-dione 在 吡啶 作用下， 反应 1.0h， 生成 (1R,2S)-2-(1-methylethoxycarbonyl)-1-phenyl-1-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis, stereochemistry, and chiroptical spectra of cyclopropyl lactones and thionolactones

  摘要：

  Several optically active substituted 3-oxabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues were synthesized, and their circular dichroism spectra are reported. It was found that the n-pi* Cotton effect sign is determined by the helicity of an inherently chiral chromophore formed by the lactone or thiolactone group and the cyclopropyl moiety. The pi-pi* Cotton effect of thiocarbonyl compounds shows opposite sign to that observed for the lowest energy transition. The crystal structures of two compounds were solved to establish their molecular geometries. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00419-3

文献信息

• Synthesis, stereochemistry, and chiroptical spectra of cyclopropyl lactones and thionolactones
  作者：Maria J. Milewska、Maria Gdaniec、Tadeusz Poloński

  DOI：10.1016/0957-4166(96)00419-3

  日期：1996.11

  Several optically active substituted 3-oxabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues were synthesized, and their circular dichroism spectra are reported. It was found that the n-pi* Cotton effect sign is determined by the helicity of an inherently chiral chromophore formed by the lactone or thiolactone group and the cyclopropyl moiety. The pi-pi* Cotton effect of thiocarbonyl compounds shows opposite sign to that observed for the lowest energy transition. The crystal structures of two compounds were solved to establish their molecular geometries. Copyright (C) 1996 Elsevier Science Ltd
• 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.