3α,4α,5α-4-piperidino-3,5-cyclopiperidine-4-carboxamide | 154905-60-9

• 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: 3α,4α,5α-4-piperidino-3,5-cyclopiperidine-4-carboxamide
• 英文别名: 1α,5α,6α-6-piperidino-3-azabicyclo<3.1.0>hexane-6-carboxamide
• CAS: 154905-60-9
• 化学式: C₁₁H₁₉N₃O
• 分子量: 209.291
• InChiKey: XPAVVQPXYWGYAK-JZYVYDRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.36
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-氯-4'-氟苯丁酮 、 3α,4α,5α-4-piperidino-3,5-cyclopiperidine-4-carboxamide 在 sodium carbonate 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以39%的产率得到1α,5α,6α-3-<4-(4-fluorophenyl)-4-oxobutyl>-6-piperidino-3-azabicyclo<3.1.0>hexane-6-carboxamide
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - XV. Synthesis of conformationally rigid analogues of [1,4′-bipiperidine]-4′-carboxamide - a common pharmacophoric group

  摘要：

  6-Piperidino-3-azabicyclo[3.1.0]hexane-6-carboxamide diastereomers 5 and 7 represent conformationally rigid analogues of the pharamacophoric group 1. Compounds 5 and 7 were synthesized with high stereoselectivity via chloroenamines 12a and 13b, respectively. Introduction of a 4-(4-flurophenyl)-4-oxobutyl moiety in 5 and 7 led to derivatives 6 and 8 which correspond to rigid conformers of Pipamperone 2, a neuroleptic drug. An X-ray structure analysis was performed for compound 6; configuration and conformation of 5-8 were determined H-1 NMR spectroscopically. 3',5'-Cyclopipamperone diastereomers 6 and 8 showed different affinities to dopamine receptors D-2L and D-3.

  DOI：

  10.1016/s0040-4020(01)81111-x
• 作为产物：
  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

文献信息

• Schlag Wolf-Ruediger, Vilsmaier Elmar, Maas Gerhard, Tetrahedron, 50 (1994) N 10, S 3123-3138
  作者：Schlag Wolf-Ruediger, Vilsmaier Elmar, Maas Gerhard

  DOI：——

  日期：——