2-[benzyl]-4α-({[3,5-bis(trifluoromethyl)benzyl]oxy}methyl)-7β-methyl-4β-phenyl-3aα,7aα-octahydro-1H-pyrrolo[3,4-c]pyridin-7α-ol

• 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: 2-[benzyl]-4α-({[3,5-bis(trifluoromethyl)benzyl]oxy}methyl)-7β-methyl-4β-phenyl-3aα,7aα-octahydro-1H-pyrrolo[3,4-c]pyridin-7α-ol
• 英文别名: (3aS,4S,7R,7aR)-2-benzyl-4-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-7-methyl-4-phenyl-1,3,3a,5,6,7a-hexahydropyrrolo[3,4-c]pyridin-7-ol
• 化学式: C₃₁H₃₂F₆N₂O₂
• 分子量: 578.598
• InChiKey: JOXCCFSAYVTGMC-ICYKMPLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.7
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲酸铵 、 2-[benzyl]-4α-({[3,5-bis(trifluoromethyl)benzyl]oxy}methyl)-7β-methyl-4β-phenyl-3aα,7aα-octahydro-1H-pyrrolo[3,4-c]pyridin-7α-ol 在 palladium on activated charcoal 作用下， 以 甲醇 为溶剂， 以98%的产率得到4α-({[3,5-bis(trifluoromethyl)benzyl]oxy}methyl)-7β-methyl-4β-phenyl-3aα,7aα-octahydro-1H-pyrrolo[3,4-c]pyridin-7α-ol formate salt
  参考文献：
  名称：

  Generation of Cyclopenta[c]piperidines and Pyrrolo[3,4-c]piperidines—Potential Substance P Antagonists—from Adducts of Cyclic Dienophiles and 5-Chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one

  摘要：

  1,1,4,4-Tetrasubstituted cyclopenta[c]piperidines and the corresponding 4,4,7,7-pyrrolo[3,4-c]piperidines have been synthesised via cycloaddition of 5-chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one with cyclopentene and 3-pyrroline derivatives, respectively, followed by reductive opening of the lactone-bridged adducts. The axial-equatorial conformational preferences of the substituents in these cis-fused bicyclic systems were opposite to those for the monocyclic piperidine analogues. The specific array of functional groups in the bicyclic aminoalcohols was used to accommodate, in stereocontrolled fashion, variable pharmacophoric groups that are of interest for substance P antagonist activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00559-7
• 作为产物：
  描述：

  5-氯-6-甲基-3-苯基-1,4-恶嗪-2-酮 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 2-[benzyl]-4α-({[3,5-bis(trifluoromethyl)benzyl]oxy}methyl)-7β-methyl-4β-phenyl-3aα,7aα-octahydro-1H-pyrrolo[3,4-c]pyridin-7α-ol
  参考文献：
  名称：

  Generation of Cyclopenta[c]piperidines and Pyrrolo[3,4-c]piperidines—Potential Substance P Antagonists—from Adducts of Cyclic Dienophiles and 5-Chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one

  摘要：

  1,1,4,4-Tetrasubstituted cyclopenta[c]piperidines and the corresponding 4,4,7,7-pyrrolo[3,4-c]piperidines have been synthesised via cycloaddition of 5-chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one with cyclopentene and 3-pyrroline derivatives, respectively, followed by reductive opening of the lactone-bridged adducts. The axial-equatorial conformational preferences of the substituents in these cis-fused bicyclic systems were opposite to those for the monocyclic piperidine analogues. The specific array of functional groups in the bicyclic aminoalcohols was used to accommodate, in stereocontrolled fashion, variable pharmacophoric groups that are of interest for substance P antagonist activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00559-7