ethyl 1α,5α,6α-6-cyano-6-piperidino-3-azabicyclo<3.1.0>hexane-3-carboxylate | 154822-89-6

• 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: ethyl 1α,5α,6α-6-cyano-6-piperidino-3-azabicyclo<3.1.0>hexane-3-carboxylate
• CAS: 154822-89-6
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: BQJFFYRJCZFNQX-IMRBUKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  56.57
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1α,5α,6α-6-cyano-6-piperidino-3-azabicyclo<3.1.0>hexane-3-carboxylate 在 碘代三甲硅烷 、 硫酸 、 sodium carbonate 、 potassium iodide 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 79.5h， 生成 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：

  ethyl 1,2,3,6-tetrahydro-4-piperidino-pyridine-1-carboxylate 在 N-氯代丁二酰亚胺 、 sodium 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 ethyl 1α,5α,6α-6-cyano-6-piperidino-3-azabicyclo<3.1.0>hexane-3-carboxylate
  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：——