3α,4β,5α-4-amino-1-benzyl-3,5-cyclopiperidine-4-carboxamide | 164799-12-6

• 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: 3α,4β,5α-4-amino-1-benzyl-3,5-cyclopiperidine-4-carboxamide
• CAS: 164799-12-6
• 化学式: C₁₃H₁₇N₃O
• 分子量: 231.297
• InChiKey: HCELORXOJFGVMV-PTEHBNRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3α,4β,5α-4-amino-1-benzyl-3,5-cyclopiperidine-4-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以69%的产率得到3α,4β,5α-4-amino-3,5-cyclopiperidine-4-carboxamide
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis — XVII. 3,5-Cyclopiperidine-4-carboxamides with an unsubstituted 4-amino moiety — A synthetic and a conformational study

  摘要：

  4-Amino-3,5-cyclopiperidine compounds 4a, 4b and 11 with unsubstituted amino moieties in 1- and/or Q-position were prepared via tribenzyl derivative 10 by selective removal of the protecting groups. The preference of a cyclopiperidine boat conformation of diamines 4a, 4b and 11 in solution was indicated by H-1 NMR spectroscopy. X-Ray structural analysis of carboxamide 4a established the presence of both a chair and a boat cyclopiperidine molecule in the solid state. Some selected conformations of 1-methyl-4-amino-3,5-cyclopiperidine 16 were studied by HF/6-31 G(*) calculations.

  DOI：

  10.1016/0040-4020(95)00092-m
• 作为产物：
  描述：

  3α,4β,5α-1-benzyl-4-(dibenzylamino)-3,5-cyclopiperidine-4-carbonitrile 在 硫酸 作用下， 反应 1.0h， 以48%的产率得到3α,4β,5α-4-amino-1-benzyl-3,5-cyclopiperidine-4-carboxamide
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis — XVII. 3,5-Cyclopiperidine-4-carboxamides with an unsubstituted 4-amino moiety — A synthetic and a conformational study

  摘要：

  4-Amino-3,5-cyclopiperidine compounds 4a, 4b and 11 with unsubstituted amino moieties in 1- and/or Q-position were prepared via tribenzyl derivative 10 by selective removal of the protecting groups. The preference of a cyclopiperidine boat conformation of diamines 4a, 4b and 11 in solution was indicated by H-1 NMR spectroscopy. X-Ray structural analysis of carboxamide 4a established the presence of both a chair and a boat cyclopiperidine molecule in the solid state. Some selected conformations of 1-methyl-4-amino-3,5-cyclopiperidine 16 were studied by HF/6-31 G(*) calculations.

  DOI：

  10.1016/0040-4020(95)00092-m