1,4-bis(3-chlorophenyl)-2-nitro-9H-carbazole | 1357386-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,4-bis(3-chlorophenyl)-2-nitro-9H-carbazole
• CAS: 1357386-04-9
• 化学式: C₂₄H₁₄Cl₂N₂O₂
• 分子量: 433.293
• InChiKey: UZIJKUZGZFVFLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 在 zinc diacetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以29%的产率得到1,4-bis(3-chlorophenyl)-3-nitro-9H-carbazole
  参考文献：
  名称：

  An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes

  摘要：

  The multifaceted behavior of nitrobutadienes deriving from the initial ring-opening of nitrothiophenes finds a further clear-cut example in their Michael-type acceptor reactivity towards indole. Thus, depending on the starting diene, either newly-functionalized indoles or carbazoles are produced, the latter as the result of an appealing double (intermolecular + intramolecular) Michael-type addition to a nitrovinylic moiety. The outcome encompasses motifs for both mechanistic and synthetic interest in the field of heterocycles endowed with possible pharmacological activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.137

文献信息

• A straight access to functionalized carbazoles by tandem reaction between indole and nitrobutadienes
  作者：Lara Bianchi、Massimo Maccagno、Marcella Pani、Giovanni Petrillo、Carlo Scapolla、Cinzia Tavani

  DOI：10.1016/j.tet.2015.05.046

  日期：2015.9

  substituted 1,3-butadienes produce poly-functionalized carbazoles through a double (inter-+intra-molecular) conjugate addition, followed by aromatization of the newly built ring. Significance is attached to the results obtained in fluorinated solvents such as trifluoroethanol, whereby a mild process, with no need for catalysis, overcomes some practical difficulties otherwise limiting the scope of the reaction

  作为对从硝基噻吩的开环获得的硝基丁二烯结构单元的合成开发的研究的继续，我们在本文中报道了它们与π-亲核吲哚的反应。由于它们具有双迈克尔受体性质，因此，2,3-二硝基和2-硝基-3-苯基磺酰基取代的1,3-丁二烯可通过两次（分子间+分子内）共轭加成，然后进行芳构化来生产多官能化咔唑。新建的戒指。在氟化溶剂（如三氟乙醇）中获得的结果具有重要意义，因此，不需要催化的温和过程克服了一些实际困难，否则会限制反应范围。除了机械方面，反应还包含了一些合成兴趣的主题，
• An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes
  作者：Lara Bianchi、Gianluca Giorgi、Massimo Maccagno、Giovanni Petrillo、Carlo Scapolla、Cinzia Tavani

  DOI：10.1016/j.tetlet.2011.11.137

  日期：2012.2

  The multifaceted behavior of nitrobutadienes deriving from the initial ring-opening of nitrothiophenes finds a further clear-cut example in their Michael-type acceptor reactivity towards indole. Thus, depending on the starting diene, either newly-functionalized indoles or carbazoles are produced, the latter as the result of an appealing double (intermolecular + intramolecular) Michael-type addition to a nitrovinylic moiety. The outcome encompasses motifs for both mechanistic and synthetic interest in the field of heterocycles endowed with possible pharmacological activity. (C) 2011 Elsevier Ltd. All rights reserved.