N-(2-phenylethynyl)phenyl-2-azidoacetamide | 1466534-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-phenylethynyl)phenyl-2-azidoacetamide
• 英文别名: 2-azido-N-[2-(2-phenylethynyl)phenyl]acetamide
• CAS: 1466534-24-6
• 化学式: C₁₆H₁₂N₄O
• 分子量: 276.297
• InChiKey: AOHRZPOUQRWSQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-phenylethynyl)phenyl-2-azidoacetamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以60%的产率得到2-phenyl-1,2,3-triazolo[5,1-d][1,4]benzodiazepin-2-one
  参考文献：
  名称：

  Three-Step Synthesis of Triazolobenzodiazepinones via Sonogashira/Huisgen Protocol

  摘要：

  The sequential Sonogashira coupling/intramolecular azide cycloaddition (Huisgen cycloaddition) protocol was performed onto N-(2-iodophenyl)-2-azidoacetamide as the acyclic precursor giving tricyclic 1,2,3-triazolo-[5,1-d][1,4]benzodiazepin-2-ones. These target products were thus obtained through a three-step synthesis in variable yields depending upon the substituent placed onto the acetylenic counterpart. The influence of catalyst concentration, reaction temperature and reaction medium upon cycloadduct yields were also studied.

  DOI：

  10.3987/com-13-12752
• 作为产物：
  描述：

  N-(2-iodophenyl)-2-azidoacetamide 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以67%的产率得到N-(2-phenylethynyl)phenyl-2-azidoacetamide
  参考文献：
  名称：

  Three-Step Synthesis of Triazolobenzodiazepinones via Sonogashira/Huisgen Protocol

  摘要：

  The sequential Sonogashira coupling/intramolecular azide cycloaddition (Huisgen cycloaddition) protocol was performed onto N-(2-iodophenyl)-2-azidoacetamide as the acyclic precursor giving tricyclic 1,2,3-triazolo-[5,1-d][1,4]benzodiazepin-2-ones. These target products were thus obtained through a three-step synthesis in variable yields depending upon the substituent placed onto the acetylenic counterpart. The influence of catalyst concentration, reaction temperature and reaction medium upon cycloadduct yields were also studied.

  DOI：

  10.3987/com-13-12752

文献信息

• Three-Step Synthesis of Triazolobenzodiazepinones via Sonogashira/Huisgen Protocol
  作者：Giorgio Molteni

  DOI：10.3987/com-13-12752

  日期：——

  The sequential Sonogashira coupling/intramolecular azide cycloaddition (Huisgen cycloaddition) protocol was performed onto N-(2-iodophenyl)-2-azidoacetamide as the acyclic precursor giving tricyclic 1,2,3-triazolo-[5,1-d][1,4]benzodiazepin-2-ones. These target products were thus obtained through a three-step synthesis in variable yields depending upon the substituent placed onto the acetylenic counterpart. The influence of catalyst concentration, reaction temperature and reaction medium upon cycloadduct yields were also studied.