N-((E)-1-Ethyl-3-phenyl-allyl)-acetamide | 138943-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((E)-1-Ethyl-3-phenyl-allyl)-acetamide
• 英文别名: N-[(E)-1-phenylpent-1-en-3-yl]acetamide
• CAS: 138943-48-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: VXPPGWLRTZVIHR-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-phenylpent-1-en-3-yl acetate 、 乙腈 在 CoCl₂ 溶剂黄146 作用下， 以76%的产率得到N-((E)-1-Ethyl-3-phenyl-allyl)-acetamide
  参考文献：
  名称：

  Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles

  摘要：

  Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers. Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane. The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures. The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium. Some preliminary studies indicate that these reactions are proceeding via an pi-allyl complex or tight ion pair rather than a [3,3] sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.

  DOI：

  10.1021/jo00114a013

文献信息

• Cobalt(II) chloride catalysed conversion of allylic alcohols to rearranged allylic amides
  作者：Naresh K. Nayyar、M. Madhava Reddy、Javed Iqbal

  DOI：10.1016/0040-4039(91)80456-g

  日期：1991.11

  Secondary and tertiary allylic alcohols can be converted to the corresponding allylically rearranged amides and acetates in presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas the secondary ones yield a mixture of regioisomers.

  可以在催化量的氯化钴（II）和乙酸酐在乙腈中存在的情况下，将仲和叔烯丙基醇转化为相应的烯丙基重排的酰胺和乙酸酯。叔醇进行完全重排，而仲醇产生区域异构体的混合物。
• Co(III)DMG-Catalyzed Synthesis of Allylamides from Allyl Alcohols and Acetonitrile
  作者：Manoj Mukhopadhyay、Javed Iqbal

  DOI：10.1021/jo960557q

  日期：1997.3.1
• Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles
  作者：Manoj Mukhopadhyay、M. Madhava Reddy、G. C. Maikap、Javed Iqbal

  DOI：10.1021/jo00114a013

  日期：1995.5

  Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers. Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane. The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures. The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium. Some preliminary studies indicate that these reactions are proceeding via an pi-allyl complex or tight ion pair rather than a [3,3] sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.