4-nitro-N-(1-tosylmethyl)benzamide | 57428-44-1

• 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: 4-nitro-N-(1-tosylmethyl)benzamide
• 英文别名: N-Tosylmethyl-p-nitrobenzamid；N-[(4-methylphenyl)sulfonylmethyl]-4-nitrobenzamide
• CAS: 57428-44-1
• 化学式: C₁₅H₁₄N₂O₅S
• 分子量: 334.353
• InChiKey: ZFVAGMJAXVRJLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 hydrofluoroboric acid 、 水 、 caesium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 0.91h， 生成 4-nitro-N-(1-tosylmethyl)benzamide
  参考文献：
  名称：

  A Transition-Metal-Free Synthesis of Arylcarboxyamides from Aryl Diazonium Salts and Isocyanides

  摘要：

  A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium intermediate.

  DOI：

  10.1021/ol4017244

文献信息

• A Transition-Metal-Free Synthesis of Arylcarboxyamides from Aryl Diazonium Salts and Isocyanides
  作者：Zhonghua Xia、Qiang Zhu

  DOI：10.1021/ol4017244

  日期：2013.8.16

  A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium intermediate.