(1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carbonitrile | 180684-06-4

• 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: (1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carbonitrile
• CAS: 180684-06-4
• 化学式: C₁₈H₂₃N₃
• 分子量: 281.401
• InChiKey: JURCKGDJZYHDKM-PIIMJCKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  30.27
• 氢给体数：
  0.0
• 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-carbonitrile 在 palladium on activated charcoal ammonium hydroxide 、 硫酸 、 氢气 、 sodium carbonate 、 potassium iodide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 67.75h， 生成 (1S,5R,6S)-3-(3-Cyano-3,3-diphenyl-propyl)-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
• 作为产物：
  描述：

  1'-Benzyl-3'-chloro-3,4,5,6,1',2',3',6'-octahydro-2H-[1,4']bipyridinyl 在 氟磺酸 作用下， 以 水 、 乙腈 为溶剂， 反应 7.0h， 生成 (1S,5R,6S)-3-Benzyl-6-piperidin-1-yl-3-aza-bicyclo[3.1.0]hexane-6-carbonitrile
  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