(1S,5R)-3-methyl-3-azabicyclo[3.1.0]hexan-2-one | 175275-35-1

• 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,5R)-3-methyl-3-azabicyclo[3.1.0]hexan-2-one
• CAS: 175275-35-1
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: DFVMHYWYOGFIQK-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (1S,5R)-3-methyl-3-azabicyclo[3.1.0]hexan-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以56%的产率得到(1S,5R)-3-methyl-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：

  (1S,2R)-2-Hydroxymethyl-cyclopropanecarboxylic acid isopropyl ester 在 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 11.0h， 生成 (1S,5R)-3-methyl-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

• Highly Enantioselective Intramolecular Cyclopropanation Reactions of <i>N</i>-Allylic-<i>N</i>-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates
  作者：Michael P. Doyle、Alexey V. Kalinin

  DOI：10.1021/jo9519219

  日期：1996.1.1

  Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N-methyldiazoacetamide, catalysis by dirhodium(II) tetrakis[methyl 2-oxapyrrolidine-5(S)-carboxylate], Rh-2(5(S)-MEPY)(4), achieved the highest yield and enantioselectivity (93% eel. Dirhodium(II) tetrakis[methyl 2-oxo-1-(3-phenylpropanoyl)imidazolidin-4(S)-carboxylate] Rh-2(4S)-MPPIM)(4), was preferred for substituted N-allylic-N-methyldiazoacetamides from which 92-95% ee's were obtained in intramolecular cyclopropanation reactions (88-95% yields), even when the catalyst was employed in only 0.1 mol %, Competition with intramolecular dipolar cycloaddition was minimized with the use of N-methyldiazoacetamides relative to N-tert-butyldiazoacetamides.
• 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.