N'-Methyl-2,3'-bi-indolyl | 88919-85-1

• 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: N'-Methyl-2,3'-bi-indolyl
• 英文别名: 1'-methyl-1H,1'H-2,3'-biindole；1'-methyl-2,3'-diindolyl；2,3'-Bi-1h-indole,1'-methyl-；3-(1H-indol-2-yl)-1-methylindole
• CAS: 88919-85-1
• 化学式: C₁₇H₁₄N₂
• 分子量: 246.312
• InChiKey: VIGIPFIQWURSOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  141-144 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  504.6±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.7
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以80 mg的产率得到N'-Methyl-2,3'-bi-indolyl
  参考文献：
  名称：

  Reactions of 2-(Lithiomethyl)phenyl Isocyanides with Methyl 1-Methylindole-3-carboxylate: Flaborations of the Adducts to 5H-Benz[2,3]azepino[5,6-c]indol-12-one and 2,3’-Biindolyl Derivatives

  摘要：

  It has been found that when 2-(lithiomethyl)phenyl isocyanides were allowed to react with methyl 1-methylindole-3-carboxylate, the corresponding 1,4-and/or 1,2-adducts were obtained. The 1,4-adducts could be transformed into 6,11-dihydro-5H-benz[2,3]azepino[5,6-b]indol-12-ones derivatives by acid hydrolysis, followed by lactamization and subsequent dehydrozgenation. The transformation of the 1,2-adducts into 2,3'-biindolyls was accomplished by a sequential treatment with hydrochloric acid and aqueous sodium hydroxide.

  DOI：

  10.3987/com-09-11778

文献信息

• Synthesis and spectroscopic characteristics of 2,3,-biindolyl and 2,2-indolylpyrroles
  作者：Vittorio Bocchi、Gerardo Palla

  DOI：10.1016/0040-4020(84)85007-3

  日期：1984.1

  A general and selective method has been achieved to synthesize 2,3'- biindolyls and 2,2'-indolylpyrroles through an acid catalysed reaction of 3-bromoindoles with indoles or pyroles. I.R., 1H-NMR, 13C-NMR and MS data of the dimers are also reported.

  已经实现了通过3-溴吲哚与吲哚或吡咯的酸催化反应来合成2,3'-联吲哚基和2,2'-吲哚基吡咯的通用且选择性的方法。还报道了二聚体的IR，1 H-NMR，13 C-NMR和MS数据。
• A new procedure for the synthesis of 2-(2-indolyl)pyrroles, 2,3′-bi-indolyls, and 2-(3-indolyl)-3-(2-indolyl)indoles
  作者：Vittorio Bocchi、Gerardo Palla

  DOI：10.1039/c39830001074

  日期：——

  The 3-bromoindoles were found to react with pyrroles and indoles, in the presence of protic or Lewis acids, to give 2-(2-indolyl)pyrroles, 2,3′-bi-indolyls, and trimetic products such as 2-(3-indolyl)-3-(2-indolyl)indoles.

  发现3-溴吲哚在质子酸或路易斯酸存在下与吡咯和吲哚反应，生成2-（2-吲哚基）吡咯，2,3'-联吲哚基和三官能产物，例如2-（ 3-吲哚基）-3-（2-吲哚基）吲哚。
• Modular Counter-Fischer–Indole Synthesis through Radical-Enolate Coupling
  作者：Hyunho Chung、Jeongyun Kim、Gisela A. González-Montiel、Paul Ha-Yeon Cheong、Hong Geun Lee

  DOI：10.1021/acs.orglett.1c00003

  日期：2021.2.5
• BOCCHI, V.;PALLA, G., TETRAHEDRON, 1984, 40, N 17, 3251-3256
  作者：BOCCHI, V.、PALLA, G.

  DOI：——

  日期：——
• Reactions of 2-(Lithiomethyl)phenyl Isocyanides with Methyl 1-Methylindole-3-carboxylate: Flaborations of the Adducts to 5H-Benz[2,3]azepino[5,6-c]indol-12-one and 2,3’-Biindolyl Derivatives
  作者：Kazuhiro Kobayashi、Shuhei Fukamachi、Hisatoshi Konishi、Daisuke Nakai

  DOI：10.3987/com-09-11778

  日期：——

  It has been found that when 2-(lithiomethyl)phenyl isocyanides were allowed to react with methyl 1-methylindole-3-carboxylate, the corresponding 1,4-and/or 1,2-adducts were obtained. The 1,4-adducts could be transformed into 6,11-dihydro-5H-benz[2,3]azepino[5,6-b]indol-12-ones derivatives by acid hydrolysis, followed by lactamization and subsequent dehydrozgenation. The transformation of the 1,2-adducts into 2,3'-biindolyls was accomplished by a sequential treatment with hydrochloric acid and aqueous sodium hydroxide.