N-benzoyl-N-ethylcyanamide | 1404073-93-3

• 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-benzoyl-N-ethylcyanamide
• 英文别名: N-cyano-N-ethylbenzamide
• CAS: 1404073-93-3
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: IDTRNPRUVKACRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,6-己二胺 、 N-benzoyl-N-ethylcyanamide 在 二苯二硫醚 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 60.0h， 以65%的产率得到1,1'-(1,6-hexylene)-bis(2-(phenylcarbonyl)-3-ethylguanidine)
  参考文献：
  名称：

  Rearrangements of N-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides

  摘要：

  We report a tin-free one-pot radical approach to the synthesis of N-acyl isothioureas and acylguanidines from N-acyl cyanamides. Photoactivated reduction of aromatic disulfides in the presence of Hunig's base results in hydrothiolation of the cyanamide moiety, followed by spontaneous 1,3-migration of the acyl group. Onward reaction of the isothioureas obtained with amines led to the corresponding N-acylguanidines, where the acyl group is attached to the nitrogen atom formerly at the cyano-end of the starting material.

  DOI：

  10.1021/ol3026439
• 作为产物：
  描述：

  异硫氰酸乙酯 、 苯甲酰氯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以59%的产率得到N-benzoyl-N-ethylcyanamide
  参考文献：
  名称：

  Rearrangements of N-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides

  摘要：

  We report a tin-free one-pot radical approach to the synthesis of N-acyl isothioureas and acylguanidines from N-acyl cyanamides. Photoactivated reduction of aromatic disulfides in the presence of Hunig's base results in hydrothiolation of the cyanamide moiety, followed by spontaneous 1,3-migration of the acyl group. Onward reaction of the isothioureas obtained with amines led to the corresponding N-acylguanidines, where the acyl group is attached to the nitrogen atom formerly at the cyano-end of the starting material.

  DOI：

  10.1021/ol3026439

文献信息

• Rearrangements of <i>N</i>-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides
  作者：Giovanni Maestri、Marie-Hélène Larraufie、Cyril Ollivier、Max Malacria、Louis Fensterbank、Emmanuel Lacôte

  DOI：10.1021/ol3026439

  日期：2012.11.2

  We report a tin-free one-pot radical approach to the synthesis of N-acyl isothioureas and acylguanidines from N-acyl cyanamides. Photoactivated reduction of aromatic disulfides in the presence of Hunig's base results in hydrothiolation of the cyanamide moiety, followed by spontaneous 1,3-migration of the acyl group. Onward reaction of the isothioureas obtained with amines led to the corresponding N-acylguanidines, where the acyl group is attached to the nitrogen atom formerly at the cyano-end of the starting material.