2,8-dimethyl-1-phenyl-1,8-dihydropyrrolo[2,3-b]indole-3-carbonitrile | 922184-69-8

• 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: 2,8-dimethyl-1-phenyl-1,8-dihydropyrrolo[2,3-b]indole-3-carbonitrile
• 英文别名: 2,4-dimethyl-3-phenylpyrrolo[2,3-b]indole-1-carbonitrile
• CAS: 922184-69-8
• 化学式: C₁₉H₁₅N₃
• 分子量: 285.348
• InChiKey: CYGQJMPFUKHIRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(1-methyl-1H-indol-3-yl)-3-(phenylamino)but-2-enenitrile 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到2,8-dimethyl-1-phenyl-1,8-dihydropyrrolo[2,3-b]indole-3-carbonitrile
  参考文献：
  名称：

  Synthesis of N-Substituted Indole Derivatives via PIFA-Mediated Intramolecular Cyclization

  摘要：

  A variety of N- arylated and N- alkylated indole derivatives were synthesized by way of a phenyliodine bis( trifluoroacetate) ( PIFA)- mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N- atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole- fused aromatic compounds can also be achieved by this method.

  DOI：

  10.1021/ol062288o

文献信息

• Oxidative Cyclization of 2-Aryl-3-arylamino-2-alkenenitriles to <i>N</i>-Arylindole-3-carbonitriles Mediated by NXS/Zn(OAc)₂
  作者：Qiao Yan、Ji Luo、Daisy Zhang-Negrerie、Hui Li、Xiuxiang Qi、Kang Zhao

  DOI：10.1021/jo2012187

  日期：2011.11.4

  N-arylindole-3-carbonitriles in a one-pot manner through NBS- or NCS-mediated halogenation followed by Zn(OAc)2-catalyzed intramolecular cyclization. It is postulated that the process involves the formation of arylnitrenium ion intermediates, which undergo the electrophilic aromatic substitution to give the cyclized N-arylindole product.

  通过NBS或NCS介导的卤化反应，然后通过Zn（OAc）2催化的分子内环化反应，将多种2-芳基-3-芳基氨基-2-烯腈以一锅方式转化为N-芳基吲哚-3-腈。据推测，该方法涉及形成芳基氮鎓离子中间体，该中间体经过亲电芳族取代得到环化的N-芳基吲哚产物。