1-Benzyl-3,3-(ethylenedioxy)piperidine | 127364-04-9

• 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-3,3-(ethylenedioxy)piperidine
• 英文别名: 7-benzyl-1,4-dioxa-7-aza-spiro[4.5]decane；Ketal 43；9-benzyl-1,4-dioxa-9-azaspiro[4.5]decane
• CAS: 127364-04-9
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JOMDFBQUFPBYDS-UHFFFAOYSA-N

物化性质

• 沸点：
  332.3±32.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Benzyl-3,3-(ethylenedioxy)piperidine 在 双氧水 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 1-Benzyl-3,3-(ethylenedioxy)-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
• 作为产物：
  描述：

  1-苄基-3-哌啶酮 、 乙二醇 在 盐酸 作用下， 以 氯仿 为溶剂， 生成 1-Benzyl-3,3-(ethylenedioxy)piperidine
  参考文献：
  名称：

  Arya,V.P. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 635 - 640

  摘要：

  DOI：

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：——
• 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.
• Arya,V.P. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 635 - 640
  作者：Arya,V.P. et al.

  DOI：——

  日期：——