3-phenyl-2-(m-tolyl)-1H-indole | 1215004-60-6

• 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: 3-phenyl-2-(m-tolyl)-1H-indole
• 英文别名: 2-(3-methylphenyl)-3-phenyl-1H-indole
• CAS: 1215004-60-6
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: AQMVMKUYTLPZSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-(m-tolyl)-1H-indole 以 乙醇 为溶剂， 反应 11.0h， 以70%的产率得到7-methyl-9H-dibenzo[a,c]carbazole
  参考文献：
  名称：

  通过紫外光照射 2,3-二苯基-1H-吲哚的无氧化剂和无催化剂合成二苯并[a,c]咔唑

  摘要：

  描述了在紫外线照射 (λ = 365 nm) 下通过在乙醇中环化 2,3-二苯基-1H-吲哚以及析氢来合成二苯并 [a, c] 咔唑的有效方法。该方法具有反应条件温和、不需要任何氧化剂和催化剂、释放的唯一副产物氢气的优点。值得注意的是，机理研究证实了反式-4b,8a-二氢-9H-二苯并[a,c]咔唑中间体可以转化为顺式-4b,8a-二氢-9H-二苯并[a,c]咔唑，其依赖于吲哚环的氮原子。随后进行分子内脱氢，产生二苯并[a,c]咔唑。

  DOI：

  10.1055/a-1677-4881
• 作为产物：
  描述：

  2-氨基二苯甲酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 26.0h， 生成 3-phenyl-2-(m-tolyl)-1H-indole
  参考文献：
  名称：

  A concise protocol for the synthesis of 2-alkenylindoles through [4 + 1] annulation of aminobenzyl phosphonium salts with acrylaldehydes

  摘要：

  A concise and efficient protocol for the synthesis of various 2-alkenylindole derivatives is developed through [4 + 1] annulation starting from aminobenzyl phosphonium salts and cinnamaldehydes.

  DOI：

  10.1039/d4gc02859g

文献信息

• Phosphine-free thiopseudourea-Pd(II) complex catalyzed Larock heteroannulation of 2-haloamines with internal alkynes
  作者：Keesara Srinivas、Parvathaneni Saiprathima、Kodicherla Balaswamy、Mandapati Mohan Rao

  DOI：10.1016/j.jorganchem.2013.05.049

  日期：2013.10

  We examined the Pd-catalyzed heteroannulation of 2-haloamines with internal alkynes under phosphine-free conditions. The thiopseudourea palladium(II) complex (5) found to be an efficient catalyst for the Pd induced heteroannulation. Achieved high turnover number for the heteroannulation reactions of internal alkynes with 2-iodoaniline. A variety of 2-bromoanilines and N-tosyl substituted 2-bromoanilines

  我们研究了在无膦条件下，Pd催化的2-卤代胺与内部炔烃的杂环化反应。发现硫代伪脲钯（II）配合物（5）是Pd诱导的异环化的有效催化剂。内部炔烃与2-碘苯胺的杂环化反应实现了高周转率。各种2-溴苯胺和N-甲苯磺酰基取代的2-溴苯胺可与不同的取代内部炔烃有效反应，以高至高收率（区域异构体比例为1：1）得到相应的吲哚。
• Practical method for synthesis of 2,3-disubstituted indole derivatives promoted by β-(benzotriazol-1-yl)allylic O-stannyl ketyl radicals
  作者：Taehoon Kim、Kyongtae Kim

  DOI：10.1016/j.tetlet.2009.12.030

  日期：2010.2

  Treatment of beta-aryl-beta-(benzotriazol-1-yl)-alpha-primary alkyl (or aryl)-alpha,beta-unsaturated ketones 1 with n-Bu3SnH (4 equiv) in a catalytic amount of AlBN in PhH at reflux afforded 3-alkyl (or aryl)-2-arylindoles 8 in good yields. However, when tert-butyl group is bonded at alpha-position, 3-acyl (or aroyl)-2-arylindoles 9 were obtained as major products along with phenanthridines 5 as minor products. (C) 2009 Elsevier Ltd. All rights reserved.
• Rhodium-Catalyzed Selective Oxidative (Spiro)annulation of 2-Arylindoles by Using Benzoquinone as a C2 or C1 Synthon
  作者：Shenghai Guo、Yangfan Liu、Lu Zhao、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.orglett.9b02336

  日期：2019.8.16

  Rhodium-catalyzed substrate-tunable oxidative annulation and spiroannulation reactions of 2-arylindoles with benzoquinone leading to 9H-dibenzo[a,c]carbazol-3-ols and new spirocyclic products are reported. Intriguingly, with 2-arylsubstituted indoles, benzoquinone could act as a C2 synthon to afford dibenzo[a,c]carbazoles. On the contrary, when 2-aryl-3-substituted indoles were used, benzoquinone switched to act as a C1 synthon to furnish spirocyclic compounds. In addition, further transformations of the obtained products demonstrate the synthetic utility of the present protocol.