Ethyl 1-Benzyl-6-cyano-3-piperidinecarboxylate | 132462-28-3

• 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 1-Benzyl-6-cyano-3-piperidinecarboxylate
• 英文别名: ethyl (3R,6S)-1-benzyl-6-cyanopiperidine-3-carboxylate
• CAS: 132462-28-3；132462-32-9
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: HAILJONBXUFSOI-CABCVRRESA-N

物化性质

• 沸点：
  399.8±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氰化钾 、 1-苄基-3-哌啶甲酸乙酯 在 mercury(II) diacetate 作用下， 生成 Ethyl 1-Benzyl-6-cyano-3-piperidinecarboxylate 、 3-Piperidinecarboxylic acid, 6-cyano-1-(phenylmethyl)-, ethyl ester, cis-
  参考文献：
  名称：

  Regioselective oxidation of piperidine-3 derivatives: a synthetic route to 2,5-substituted piperidines

  摘要：

  Mercuric acetate oxidation of 1-benzyl-3,3-(ethylenedioxy)piperidine (1) and of 3-CO2Et- and 3-CH2OH-substituted piperidines 7-9 was shown to occur regioselectively at the 6-position. Trapping of the resulting 6-iminium ions with cyanide yielded the corresponding 5-substituted 2-piperidinecarbonitriles 5, 10, and 11. However, the 2-iminium ion was formed in the reaction of the N-oxide of 1 with trifluoroacetic anydride; with cyanide this afforded the regioisomeric 3,3-(ethylenedioxy)-2-piperidinecarbonitrile (2). Plausible mechanisms are advanved to explain this contrasting behavior. 1-Benzyl-5,5-(ethylenedioxy)-2-piperidinecarbonitrile (5) was transformed into other piperidine-2,5 derivatives by reaction of the alpha-amino nitrile anion with electrophoresis, followed by reductive decyanation.

  DOI：

  10.1021/jo00007a025

文献信息

• Regioselective oxidation of piperidine-3 derivatives: a synthetic route to 2,5-substituted piperidines
  作者：Frans Compernolle、M. Ashty Saleh、Stefan Van den Branden、Suzanne Toppet、Georges Hoornaert

  DOI：10.1021/jo00007a025

  日期：1991.3

  Mercuric acetate oxidation of 1-benzyl-3,3-(ethylenedioxy)piperidine (1) and of 3-CO2Et- and 3-CH2OH-substituted piperidines 7-9 was shown to occur regioselectively at the 6-position. Trapping of the resulting 6-iminium ions with cyanide yielded the corresponding 5-substituted 2-piperidinecarbonitriles 5, 10, and 11. However, the 2-iminium ion was formed in the reaction of the N-oxide of 1 with trifluoroacetic anydride; with cyanide this afforded the regioisomeric 3,3-(ethylenedioxy)-2-piperidinecarbonitrile (2). Plausible mechanisms are advanved to explain this contrasting behavior. 1-Benzyl-5,5-(ethylenedioxy)-2-piperidinecarbonitrile (5) was transformed into other piperidine-2,5 derivatives by reaction of the alpha-amino nitrile anion with electrophoresis, followed by reductive decyanation.