5-cyano-1-p-tolyl-1H-indole | 1203591-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-cyano-1-p-tolyl-1H-indole
• 英文别名: N-(4-methylphenyl)-5-cyanoindole；1-(4-Methylphenyl)indole-5-carbonitrile；1-(4-methylphenyl)indole-5-carbonitrile
• CAS: 1203591-80-3
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: MGFRNRAJTVYFSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-氰基吲哚 、 对溴甲苯 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以94%的产率得到5-cyano-1-p-tolyl-1H-indole
  参考文献：
  名称：

  一种还原型氧化石墨烯制备[受电子邮件保护的] 2 O纳米粒子的一步法及其在N杂环的N-芳基化中的催化活性

  摘要：

  在室温下，通过使用1-抗坏血酸作原位还原氧化石墨烯（GO）和硫酸铜，在还原的氧化石墨烯（[电子邮件保护] 2 O NPs-RGO）纳米复合材料上制备核-壳[受电子邮件保护] 2 O纳米颗粒。还原剂，然后空气氧化铜纳米颗粒的表面。[电子邮件保护] 2 O NPs-RGO纳米复合材料的特征在于红外光谱，拉曼光谱，X射线衍射，X射线光电子能谱，透射电子显微镜和能量色散X射线光谱。最后，[电子邮件保护的] 2 O NPs-RGO纳米复合材料被用作N-芳基化反应的有效且可重复使用的非均相催化剂。N-杂环。

  DOI：

  10.1016/j.apcata.2014.04.023

文献信息

• Ligand and Cu free <i>N</i>-arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst
  作者：Abhijit Paul、Debnath Chatterjee、Srirupa Banerjee、Somnath Yadav

  DOI：10.1039/d0nj02129f

  日期：——

  the N-arylation of aromatic heterocycles like indoles and pyrroles is reported by a Pd nanocatalyst under ligand- and Cu-free conditions. The reaction conditions tolerate several functional groups and work very efficiently for aryl iodides and bromides. Aryl chlorides are also successful as the coupling partners albeit with lower yields. The methodology is also applicable for the N-arylation of aliphatic

  本文中，Pd纳米催化剂在无配体和无铜的条件下报道了芳香族杂环（如吲哚和吡咯）的N-芳基化反应。反应条件可耐受多个官能团，并且对于芳基碘化物和溴化物非常有效地起作用。芳基氯化物也成功地用作偶联伙伴，尽管收率较低。该方法还可用于脂族伯胺的N-芳基化，如苄胺与几种芳基碘化物和溴化物的反应所证明的。可回收的Pd纳米催化剂通过一种异质机理催化反应，已通过多种技术进行了证明，包括三相测试和反应混合物的原位ICP-MS分析。
• Copper(I)-2-(2′-pyridyl)benzimidazole catalyzed N-arylation of indoles
  作者：Satoshi Haneda、Yusuke Adachi、Masahiko Hayashi

  DOI：10.1016/j.tet.2009.10.014

  日期：2009.12

  CuI-2-(2′-pyridyl)benzimidazole catalyst system can serve efficiently to promote N-arylation of various indoles to afford the N-arylated indoles. The bidentate ligand, 2-(2′-pyridyl)benzimidazole was proved superior to monodentate nitrogen-based ligands and well-known bidentate ligands such as 2,2′-bipyridyl and 1,10-phenanthroline.

  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。
• Green synthesis of predominant (111) facet CuO nanoparticles: Heterogeneous and recyclable catalyst for N-arylation of indoles
  作者：Nikhil V. Suramwar、Sanjay R. Thakare、Nandkishor N. Karade、Niren T. Khaty

  DOI：10.1016/j.molcata.2012.03.017

  日期：2012.7

  Well faceted CuO nanoparticles were synthesized by thermal-assisted green strategy at reflux temperature in a short period of time. A possible growth mechanism of such highly faceted nanostructures based on typical biomolecule-crystal interactions in aqueous solution is tentatively proposed. The large surface area (223.36 m(2)/g) and rich exposed active sites are expected to endow such nanostructures with excellent performances in catalysis as demonstrated here for remarkable catalytic activity with respect to the N-arylation of indoles. Nanoparticles were characterized by X-ray diffraction, scanning electron microscopy and transmission electron microscopy. Both the activity and selectivity of the N-arylation reactions could be tuned by varying the concentration of CuO nanoparticles. Nanoparticles catalyst were recycled and reused for further catalytic reactions with minimal loss in activity. A variety of indole derivatives afforded corresponding N-arylation product with excellent yields (up to 98%). (C) 2012 Elsevier B.V. All rights reserved.