N-Phenyl-N-(α-cyanoethyl)-p-fluorobenzamide | 154319-63-8

• 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-Phenyl-N-(α-cyanoethyl)-p-fluorobenzamide
• 英文别名: N-(1-cyanoethyl)-4-fluoro-N-phenylbenzamide
• CAS: 154319-63-8
• 化学式: C₁₆H₁₃FN₂O
• 分子量: 268.29
• InChiKey: WAAGOYNPKZHMPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Phenyl-N-(α-cyanoethyl)-p-fluorobenzamide 在 双氧水 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以95%的产率得到N-(α-(Aminocarbonyl)ethyl)-N-phenyl-p-fluorobenzamide
  参考文献：
  名称：

  Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins

  摘要：

  Acyclic Reissert compounds 2 and bis(Reissert compound)s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate cr-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of alpha-amino carboxamides 9, whereas substituted analogs 7 undergo cyclization to imidazolinones 11. Hydrogen peroxide treatment of alpha-cyano carbamate Reissert compounds, substituted (13) or not (12), affords substituted hydantoins 14.

  DOI：

  10.1021/jo00084a025
• 作为产物：
  描述：

  2-(苯基氨基)丙腈 、 对氟苯甲酰氯 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 N-Phenyl-N-(α-cyanoethyl)-p-fluorobenzamide
  参考文献：
  名称：

  Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins

  摘要：

  Acyclic Reissert compounds 2 and bis(Reissert compound)s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate cr-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of alpha-amino carboxamides 9, whereas substituted analogs 7 undergo cyclization to imidazolinones 11. Hydrogen peroxide treatment of alpha-cyano carbamate Reissert compounds, substituted (13) or not (12), affords substituted hydantoins 14.

  DOI：

  10.1021/jo00084a025

文献信息

• Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins
  作者：Jean-Pierre Leblanc、Harry W. Gibson

  DOI：10.1021/jo00084a025

  日期：1994.3

  Acyclic Reissert compounds 2 and bis(Reissert compound)s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate cr-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of alpha-amino carboxamides 9, whereas substituted analogs 7 undergo cyclization to imidazolinones 11. Hydrogen peroxide treatment of alpha-cyano carbamate Reissert compounds, substituted (13) or not (12), affords substituted hydantoins 14.