1'-Benzyl-3'-chloro-3,4,5,6,1',2',3',6'-octahydro-2H-[1,4']bipyridinyl | 154822-81-8

• 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: 1'-Benzyl-3'-chloro-3,4,5,6,1',2',3',6'-octahydro-2H-[1,4']bipyridinyl
• 英文别名: 1-benzyl-3-chloro-4-piperidin-1-yl-3,6-dihydro-2H-pyridine
• CAS: 154822-81-8
• 化学式: C₁₇H₂₃ClN₂
• 分子量: 290.836
• InChiKey: MGBBRANBXNBZBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  盐酸伊立替康杂质14 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1'-Benzyl-3'-chloro-3,4,5,6,1',2',3',6'-octahydro-2H-[1,4']bipyridinyl
  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

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：——
• Functionalized chloroenamines in aminocyclopropane synthesis - XV. Synthesis of conformationally rigid analogues of [1,4′-bipiperidine]-4′-carboxamide - a common pharmacophoric group
  作者：Wolf-Rüdiger Schlag、Elmar Vilsmaier、Gerhard Maas

  DOI：10.1016/s0040-4020(01)81111-x

  日期：1994.3

  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.
• A New Access to Piperidino-cyclopiperidinecarboxamides - constrained analogues of a pharmaceutical used diaminic building block
  作者：E. Vilsmaier、Markus Grosse、Wolf-R�diger Schlag、Gunther Milch、Uwe Bergstr��er、Andreas Ritter von Onciul

  DOI：10.1002/prac.19963380190

  日期：——

  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.