(1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide | 180684-07-5

• 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,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide
• CAS: 180684-07-5
• 化学式: C₁₈H₂₅N₃O
• 分子量: 299.416
• InChiKey: OEBVKZQEIQRJJV-VQFNDLOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以59%的产率得到3α,4α,5α-4-piperidino-3,5-cyclopiperidine-4-carboxamide
  参考文献：
  名称：

  A New Access to Piperidino-cyclopiperidinecarboxamides - constrained analogues of a pharmaceutical used diaminic building block

  摘要：

  6-Piperidino-3-azabicyclo [3.1.0]hexane-6-carboxamide diastereomers 1a and 2a represent conformationally rigid analogues of 3a which is a building block in some pharmaceutical compounds. A new access to these compounds 1a and 2a was found via the cleavage of bicyclic N,N-acetal 6 with hydrocyanic acid as the stereodetermining step. Reaction of derivatives 1a and 2a with bromodiphenyl-butyronitrile 14 gave cyclopiritramide isomers 1c and 2c, respectively. Qualitative preliminary investigations showed different affinities of 1c and 2c to the opiate-mu receptor. These results were discussed on the basis of an X-ray structural analysis of cyclopiritramide isomer 2c.1-Benzylcyclopiperidine derivatives 1d and 2d were used as model systems for studying the conformation of cyclopiritramide isomer 1c and 2c, respectively.

  DOI：

  10.1002/prac.19963380190
• 作为产物：
  描述：

  (1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carbonitrile 在 ammonium hydroxide 、 硫酸 作用下， 生成 (1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide
  参考文献：
  名称：

  A New Access to Piperidino-cyclopiperidinecarboxamides - constrained analogues of a pharmaceutical used diaminic building block

  摘要：

  6-Piperidino-3-azabicyclo [3.1.0]hexane-6-carboxamide diastereomers 1a and 2a represent conformationally rigid analogues of 3a which is a building block in some pharmaceutical compounds. A new access to these compounds 1a and 2a was found via the cleavage of bicyclic N,N-acetal 6 with hydrocyanic acid as the stereodetermining step. Reaction of derivatives 1a and 2a with bromodiphenyl-butyronitrile 14 gave cyclopiritramide isomers 1c and 2c, respectively. Qualitative preliminary investigations showed different affinities of 1c and 2c to the opiate-mu receptor. These results were discussed on the basis of an X-ray structural analysis of cyclopiritramide isomer 2c.1-Benzylcyclopiperidine derivatives 1d and 2d were used as model systems for studying the conformation of cyclopiritramide isomer 1c and 2c, respectively.

  DOI：

  10.1002/prac.19963380190