(2-azidophenyl)acetonitrile | 897663-71-7

• 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: (2-azidophenyl)acetonitrile
• 英文别名: 2-(2-Azidophenyl)acetonitrile
• CAS: 897663-71-7
• 化学式: C₈H₆N₄
• 分子量: 158.162
• InChiKey: GDJAYHQCIQXWPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-azidophenyl)acetonitrile 在 三乙基硅烷 、 indium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2-aminoindole
  参考文献：
  名称：

  Reaction of Azides with Dichloroindium Hydride:  Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium−Aminyl Radicals

  摘要：

  Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. gamma-Azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.

  DOI：

  10.1021/ol0606637
• 作为产物：
  描述：

  2-氨基苯乙腈 在 sodium azide 作用下， 以 水 为溶剂， 反应 0.75h， 以60%的产率得到(2-azidophenyl)acetonitrile
  参考文献：
  名称：

  Reaction of Azides with Dichloroindium Hydride:  Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium−Aminyl Radicals

  摘要：

  Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. gamma-Azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.

  DOI：

  10.1021/ol0606637

文献信息

• Access to 1<i>H</i>-indazoles, 1<i>H</i>-benzoindazoles and 1<i>H</i>-azaindazoles from (het)aryl azides: a one-pot Staudinger-aza-Wittig reaction leading to N–N bond formation?
  作者：T. Alaime、M. Daniel、M.-A. Hiebel、E. Pasquinet、F. Suzenet、G. Guillaumet

  DOI：10.1039/c8cc03612h

  日期：——

  One-pot synthesis of 1H-indazole derivatives through a proposed Staudinger-aza-Wittig tandem mechanism

  一锅法合成1H-吲唑衍生物，通过提出的Staudinger-aza-Wittig串联机制。