1-isocyanato-2-(4-nitrophenylethynyl)benzene | 1190200-00-0

• 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: 1-isocyanato-2-(4-nitrophenylethynyl)benzene
• 英文别名: 1-Isocyanato-2-[2-(4-nitrophenyl)ethynyl]benzene
• CAS: 1190200-00-0
• 化学式: C₁₅H₈N₂O₃
• 分子量: 264.24
• InChiKey: HLCSXIPRNFIATE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-isocyanato-2-(4-nitrophenylethynyl)benzene 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z)-3-[1-chloro-1-(4-nitrophenyl)methylidene]indolin-2-one 、 (E)-3-[1-chloro-1-(4-nitrophenyl)methylidene]indolin-2-one
  参考文献：
  名称：

  Iron Trichloride-Promoted Cyclization of o-Alkynylaryl Isocyanates: Synthesis of 3-(Chloromethylene)oxindoles

  摘要：

  Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (2)-3-(aminomethylene)ox in doles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.

  DOI：

  10.1021/ol9014877
• 作为产物：
  描述：

  三光气 、 2-[2-(4-硝基苯基)乙炔基]苯胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 以86%的产率得到1-isocyanato-2-(4-nitrophenylethynyl)benzene
  参考文献：
  名称：

  Iron Trichloride-Promoted Cyclization of o-Alkynylaryl Isocyanates: Synthesis of 3-(Chloromethylene)oxindoles

  摘要：

  Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (2)-3-(aminomethylene)ox in doles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.

  DOI：

  10.1021/ol9014877

文献信息

• Iron Trichloride-Promoted Cyclization of <i>o</i>-Alkynylaryl Isocyanates: Synthesis of 3-(Chloromethylene)oxindoles
  作者：Guillaume Cantagrel、Benoît de Carné-Carnavalet、Christophe Meyer、Janine Cossy

  DOI：10.1021/ol9014877

  日期：2009.10.1

  Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (2)-3-(aminomethylene)ox in doles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.