1-methyl-5-(1-phenylindol-3-yl)pyrrolidin-2-one

• 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-methyl-5-(1-phenylindol-3-yl)pyrrolidin-2-one
• 英文别名: 1-methyl-5-(1-phenyl-1H-indol-3-yl)pyrrolidin-2-one；1-methyl-5-(1-phenyl-3-indolyl)-2-pyrrolidone
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: ANEZQEDDWAESJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基吡咯烷酮 在 iron(III) chloride 作用下， 以 1,2-二氯-2-甲基丙烷 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 26.0h， 生成 1-methyl-5-(1-phenylindol-3-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Iron-Catalyzed Oxidative Coupling of Alkylamides with Arenes through Oxidation of Alkylamides Followed by Friedel−Crafts Alkylation

  摘要：

  FeCL(3) in combination with t-BuOOt-Bu as an oxidant was found to be an efficient catalyst for oxidation of alkylamides to alpha-(tert-butoxy)alkylamides. FeCl(2) and CuCl showed, respectively, almost the same and slightly lower activities compared with FeCl(3) in the tert-butoxylation of N-phenylpyrrolidone (1a), whereas no tert-butoxylated product was obtained by use of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). FeCl(3) was found to be effective also as a catalyst for the Friedel-Crafts alkylation with thus obtained alpha-(tert-butoxy)alkylamides. The Friedel-Crafts alkylation proceeded smoothly also in the presence of a catalytic amount of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). In contrast, FeCl(2) and CuCl, which showed certain activity toward the tert-butoxylation, failed to promote the Friedel Crafts alkylation. Among the transition metal complexes thus far examined, only FeCl(3) showed high catalytic activities for both the oxidation and the Friedel-Crafts alkylation. The bifunctionality of FeCl(3) was utilized for the oxidative coupling of alkylamides with arenes through a tandem reaction consisting of oxidation of alkylamides to alpha-(tert-butoxy)alkylamides and the following Friedel-Crafts alkylation. The FeCl(3)-catalyzed oxidative coupling is applicable to a wide variety of alkylamides and arenes, though a combination of FeCl(3) with Fe(OTf)(3) was found to be effective for the reaction of arenes with low nucleophilicity. A Fe(II)-Fe(III) catalytic cycle is concerned with the tert-butoxylation, whereas a Fe(III) complex as a Lewis acid catalyzes the Friedel-Crafts alkylation.

  DOI：

  10.1021/jo102217m

文献信息

• Photocatalyst-Free, Visible-Light-Mediated C(sp³)–H Arylation of Amides via a Solvent-Caged EDA Complex
  作者：Jaspreet Kaur、Ahmed Shahin、Joshua P. Barham

  DOI：10.1021/acs.orglett.1c00132

  日期：2021.3.19

  A photocatalyst-free and mild visible light photochemical procedure for C(sp3)–H arylation of amides is described. The reaction proceeds via an electron donor–acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)–H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction

  描述了酰胺的C（sp 3）–H芳基化反应的无光催化剂和温和可见光光化学程序。反应通过富电子芳烃底物与贫电子过硫酸盐氧化剂之间的电子给体-受体（EDA）配合物进行。酰胺的C（sp 3）–H芳基化选择性地发生在底物最富电子的芳烃上。机理研究证实了该反应是在溶剂笼中进行的，溶剂笼中的组分紧密相邻。
• Zirconium Triflate Catalyzed Direct Coupling Reaction of Lactams with Heterocyclic Arenes under Atmospheric Oxygen
  作者：Teruhisa Tsuchimoto、Yoshitaka Ozawa、Ryoju Negoro、Eiji Shirakawa、Yusuke Kawakami

  DOI：10.1002/anie.200460429

  日期：2004.8.13
• Iron-Catalyzed Oxidative Coupling of Alkylamides with Arenes through Oxidation of Alkylamides Followed by Friedel−Crafts Alkylation
  作者：Eiji Shirakawa、Nanase Uchiyama、Tamio Hayashi

  DOI：10.1021/jo102217m

  日期：2011.1.7

  FeCL(3) in combination with t-BuOOt-Bu as an oxidant was found to be an efficient catalyst for oxidation of alkylamides to alpha-(tert-butoxy)alkylamides. FeCl(2) and CuCl showed, respectively, almost the same and slightly lower activities compared with FeCl(3) in the tert-butoxylation of N-phenylpyrrolidone (1a), whereas no tert-butoxylated product was obtained by use of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). FeCl(3) was found to be effective also as a catalyst for the Friedel-Crafts alkylation with thus obtained alpha-(tert-butoxy)alkylamides. The Friedel-Crafts alkylation proceeded smoothly also in the presence of a catalytic amount of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). In contrast, FeCl(2) and CuCl, which showed certain activity toward the tert-butoxylation, failed to promote the Friedel Crafts alkylation. Among the transition metal complexes thus far examined, only FeCl(3) showed high catalytic activities for both the oxidation and the Friedel-Crafts alkylation. The bifunctionality of FeCl(3) was utilized for the oxidative coupling of alkylamides with arenes through a tandem reaction consisting of oxidation of alkylamides to alpha-(tert-butoxy)alkylamides and the following Friedel-Crafts alkylation. The FeCl(3)-catalyzed oxidative coupling is applicable to a wide variety of alkylamides and arenes, though a combination of FeCl(3) with Fe(OTf)(3) was found to be effective for the reaction of arenes with low nucleophilicity. A Fe(II)-Fe(III) catalytic cycle is concerned with the tert-butoxylation, whereas a Fe(III) complex as a Lewis acid catalyzes the Friedel-Crafts alkylation.