1-Benzyl-5,5-(ethylenedioxy)-2-(2-phenylethyl)-2-piperidinecarbonitrile | 132462-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-Benzyl-5,5-(ethylenedioxy)-2-(2-phenylethyl)-2-piperidinecarbonitrile
• 英文别名: 9-benzyl-8-(2-phenylethyl)-1,4-dioxa-9-azaspiro[4.5]decane-8-carbonitrile
• CAS: 132462-33-0
• 化学式: C₂₃H₂₆N₂O₂
• 分子量: 362.472
• InChiKey: TUIYBRLIQPPRAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.49
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-Benzyl-5,5-(ethylenedioxy)-2-(2-phenylethyl)-2-piperidinecarbonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以89%的产率得到1-Benzyl-5,5-(ethylenedioxy)-2-(2-phenylethyl)piperidine
  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
• 作为产物：
  描述：

  1-Benzyl-3,3-(ethylenedioxy)piperidine 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 mercury(II) diacetate 、 edetate disodium 、 lithium diisopropyl amide 作用下， 以 溶剂黄146 为溶剂， 反应 4.5h， 生成 1-Benzyl-5,5-(ethylenedioxy)-2-(2-phenylethyl)-2-piperidinecarbonitrile
  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

• COMPERNOLLE, FRANS;SALEH, M. ASHTY;DEN, BRANDEN STEFAN VAN;TOPPET, SUZANN+, J. ORG. CHEM., 56,(1991) N, C. 2386-2390
  作者：COMPERNOLLE, FRANS、SALEH, M. ASHTY、DEN, BRANDEN STEFAN VAN、TOPPET, SUZANN+

  DOI：——

  日期：——