1-Benzyl-5,5-(ethylenedioxy)-2-piperidinone | 132462-22-7

• 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: 1-Benzyl-5,5-(ethylenedioxy)-2-piperidinone
• 英文别名: 9-Benzyl-1,4-dioxa-9-azaspiro[4.5]decan-8-one
• CAS: 132462-22-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: DEAXVJLYBUSQFL-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Benzyl-5,5-(ethylenedioxy)-2-piperidinone 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 7-Benzyl-8-hydroxymethyl-1,4-dioxa-7-aza-spiro[4.5]decane-8-carbonitrile
  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 mercury(II) diacetate 、 edetate disodium 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以31%的产率得到1-Benzyl-5,5-(ethylenedioxy)-2-piperidinone
  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：——