1-Azido-2-(4-ethenylphenyl)benzene | 1140969-85-2

• 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-Azido-2-(4-ethenylphenyl)benzene
• CAS: 1140969-85-2
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: YQYQQWMMKVYDDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 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：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Azido-2-(4-ethenylphenyl)benzene 在 tetrabutylammonium tricarbonylnitrosylferrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以84%的产率得到2-vinyl-9H-carbazole
  参考文献：
  名称：

  Iron-Catalyzed Intramolecular C(sp² )−H Amination

  摘要：

  AbstractThe nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C−H amination of α‐azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional‐group tolerance render this method a particularly attractive alternative to established noble‐metal‐based procedures.

  DOI：

  10.1002/anie.201510045
• 作为产物：
  描述：

  4'-ethenyl[1,1'-biphenyl]-2-amine 在 sodium nitrite 、 sodium azide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以59%的产率得到1-Azido-2-(4-ethenylphenyl)benzene
  参考文献：
  名称：

  Iron-Catalyzed Intramolecular C(sp² )−H Amination

  摘要：

  AbstractThe nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C−H amination of α‐azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional‐group tolerance render this method a particularly attractive alternative to established noble‐metal‐based procedures.

  DOI：

  10.1002/anie.201510045

文献信息

• Rh₂(II)-Catalyzed Synthesis of Carbazoles from Biaryl Azides
  作者：Benjamin J. Stokes、Brankica Jovanović、Huijun Dong、Kathleen J. Richert、Ryan D. Riell、Tom G. Driver

  DOI：10.1021/jo9002536

  日期：2009.4.17

  An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 degrees C using substoichiometric quantities of Rh-2(O2CC3F7)(4) or Rh-2(O2CC7H15)(4).
• Iron-Catalyzed Intramolecular C(sp² )−H Amination
  作者：Isabel T. Alt、Bernd Plietker

  DOI：10.1002/anie.201510045

  日期：2016.1.22

  AbstractThe nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C−H amination of α‐azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional‐group tolerance render this method a particularly attractive alternative to established noble‐metal‐based procedures.