hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-amine | 165874-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-amine
• 英文别名: (3S,4R,5R,7R)-1-azatricyclo[3.3.1.03,7]nonan-4-amine
• CAS: 165874-34-0
• 化学式: C₈H₁₄N₂
• 分子量: 138.213
• InChiKey: UVJCUZSPROORIA-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氨基-5-氯-2-甲氧基苯甲酸 、 hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-amine 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到(+)-4-amino-5-chloro-N-(hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-yl)-2-methoxybenzamide
  参考文献：
  名称：

  Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491

  摘要：

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00680-8
• 作为产物：
  描述：

  (+)-1,1-dimethylethyl-N-[[1α,4α-bis(hydroxymethyl)-3β-[[(4-methylphenyl)sulfonyl]amino]cyclopentan-2α-yl]methyl]carbamate 在 calcium 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 氨 、 乙腈 为溶剂， 反应 117.75h， 生成 hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-amine
  参考文献：
  名称：

  Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491

  摘要：

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00680-8

文献信息

• Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491
  作者：Daniel P. Becker、Robert K. Husa、Alan E. Moormann、Clara I. Villamil、Daniel L. Flynn

  DOI：10.1016/s0040-4020(99)00680-8

  日期：1999.10

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.