1-(2-methylphenyl)-1H-indole | 210162-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-methylphenyl)-1H-indole
• 英文别名: N-(2-methyl phenyl) indole；N-(2'-methylphenyl)indole；1-(2-methylphenyl)indole；N-(2-methylphenyl)indole；1-(o-tolyl)-1H-indole；1-o-tolyl-1H-indole
• CAS: 210162-61-1
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: BJNMTUGUPXMLLO-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C
• 沸点：
  347.0±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2-methylphenyl)-1H-indole 在 PPA 作用下， 反应 130.0h， 以35%的产率得到4-methyl-5H-dibenz[b,f]azepine
  参考文献：
  名称：

  1-芳基吲哚重排为5H-dibenz [b，f] a

  摘要：

  已发现1-芳基吲哚1到5H-二苯并[b，f]氮杂2的异常酸催化重排。可用于制备2。讨论了初始分子1中取代基的性质和位置对重排的影响。建议该反应的可能机理。描述了一种通过Ullmann反应通过将1-未取代的吲哚与芳基卤化物进行芳基化来制备1-芳基吲哚1c-k的简便方法。

  DOI：

  10.1016/0040-4020(94)01082-b
• 作为产物：
  描述：

  吲哚 、 2-碘代甲苯 在 potassium phosphate 、 copper(l) iodide 、 2-(2-吡啶)-苯并咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到1-(2-methylphenyl)-1H-indole
  参考文献：
  名称：

  铜（I）-2-（2'-吡啶基）苯并咪唑催化的吲哚N-芳基化

  摘要：

  CuI-2-（2'-吡啶基）苯并咪唑催化剂体系可以有效地促进各种吲哚的N-芳基化，从而得到N-芳基化的吲哚。事实证明，二齿配体2-（2'-吡啶基）苯并咪唑优于单齿氮基配体和众所周知的二齿配体，例如2,2'-联吡啶和1,10-菲咯啉。

  DOI：

  10.1016/j.tet.2009.10.014

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• Palladium-catalysed N-annulation routes to indoles: the synthesis of indoles with sterically demanding N-substituents, including demethylasterriquinone A1
  作者：Anthony J. Fletcher、Matthew N. Bax、Michael C. Willis

  DOI：10.1039/b712227f

  日期：——

  Tandem palladium-catalysed aryl and alkenyl C–N bond formation allows the synthesis of a variety of indoles bearing sterically demanding N-substituents, including the natural product demethylasterriquinone A1.

  串联钯催化的芳基和烯基C-N键形成，实现了具有空间位阻N取代基的多种吲哚合成，包括天然产物去甲基星异醌A1。
• A carbon nitride supported copper nanoparticle composite: a heterogeneous catalyst for the N-arylation of hetero-aromatic compounds
  作者：Debkumar Nandi、Samarjeet Siwal、Kaushik Mallick

  DOI：10.1039/c6nj03584a

  日期：——

  nitride supported copper nanoparticle composite (Cu–gCN) has been found to be an active catalyst for the N-arylation of hetero-aromatic systems (pyrrole, pyrazole, and substituted indole) and benzamide molecules, with high product selectivity and good to excellent yields, using substituted aryl bromide as a coupling partner. The intercalated structure and the amine functional group of the carbon nitride

  已发现石墨碳氮化物负载的铜纳米颗粒复合材料（Cu–gCN）是杂芳族体系（吡咯，吡唑和取代的吲哚）和苯甲酰胺分子的N-芳基化反应的活性催化剂，具有较高的产品选择性和良好的选择性。使用取代的芳基溴化物作为偶联伙伴可达到极好的收率。氮化碳的插入结构和胺官能团阻止了反应过程中催化活性铜物质的聚集，可循环性研究表明催化剂的性能稳定，而催化活性没有明显损失。
• Immobilized Pd(0) nanoparticles on phosphine-functionalized graphene as a highly active catalyst for Heck, Suzuki and N-arylation reactions
  作者：Reza Fareghi-Alamdari、Mohsen G. Haqiqi、Negar Zekri

  DOI：10.1039/c5nj02227d

  日期：——

  Phosphine functionalized graphene was used for the immobilization of Pd nanoparticles and utilized in C–C and C–N bond formation reactions.

  磷化功能化石墨烯被用于固定Pd纳米颗粒，并应用于C-C和C-N键形成反应。
• CuI/8-Hydroxyquinalidine Promoted N-Arylation of Indole and Azoles
  作者：Xinye Yang、Hui Xing、Ye Zhang、Yisheng Lai、Yihua Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1002/cjoc.201100433

  日期：2012.4

  An efficient catalytic system of CuI/8‐hydroxyquinalidine was developed for the coupling of aryl iodides and indole as well as some azoles. The reaction could be carried out at 90°C under the condition of relatively low catalyst loading, affording various N‐arylindoles and N‐aryl azoles in good yields. The functionalized and hindered aryl iodides were suitable substrates for this transformation.

  开发了一种有效的CuI / 8-羟基喹啉催化体系，用于偶合芳基碘化物和吲哚以及某些唑类。该反应可以在90℃下相对低的催化剂负载的条件下进行，得到各种Ñ -arylindoles和ñ -芳基以良好产率唑类。官能化和受阻的芳基碘化物是该转化的合适底物。