1-(1-(4-chlorophenyl)-2-methyl-4-(p-tolyl)-1H-pyrrol-3-yl)ethanone | 1208334-49-9

• 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-(1-(4-chlorophenyl)-2-methyl-4-(p-tolyl)-1H-pyrrol-3-yl)ethanone
• 英文别名: 1-(1-(4-Chlorophenyl)-2-methyl-4-(p-tolyl)-1h-pyrrol-3-yl) ethanone；1-[1-(4-chlorophenyl)-2-methyl-4-(4-methylphenyl)pyrrol-3-yl]ethanone
• CAS: 1208334-49-9
• 化学式: C₂₀H₁₈ClNO
• 分子量: 323.822
• InChiKey: AILSUHCERPZEGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-methyl-β-nitrostyrene 、 对氯苯胺 、 乙酰丙酮 在 3-methyl-2-(1-sulfobutyl)-1H-imidazolium hydrogen sulfate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以91%的产率得到1-(1-(4-chlorophenyl)-2-methyl-4-(p-tolyl)-1H-pyrrol-3-yl)ethanone
  参考文献：
  名称：

  酸性离子液体[BSO3HMIm]HSO4：一种新型高效催化剂，用于一锅三组分合成取代吡咯

  摘要：

  摘要 酸性离子液体 3-甲基-2-(1-磺丁基)-1H-咪唑鎓硫酸氢盐 [BSO3HMIm]HSO4 被用作一种有效的催化剂，通过一锅、三胺、硝基烯烃和 1,3-二羰基化合物的组分缩合。在乙醇中回流下获得了 72-96% 的良好收率。催化剂可以很容易地回收和循环使用多达六次，从而在不延长反应时间的情况下获得良好的收率。这种方法在大规模制备中也是有效的。该程序可以很容易地扩展为一锅四组分反应。这种离子液体催化的反应为吡咯衍生物的合成提供了一种环境友好的替代方法。

  DOI：

  10.1515/znb-2014-0108

文献信息

• Three-Component Coupling Synthesis of Diversely Substituted N-Aryl Pyrroles Catalyzed by Iron(III) Chloride
  作者：Soumen Sarkar、Krishnendu Bera、Sukhendu Maiti、Srijit Biswas、Umasish Jana

  DOI：10.1080/00397911.2011.650273

  日期：2013.6.3

  Abstract An efficient and operationally simple three-component coupling synthesis of varieties of N-aryl substituted pyrroles is described in the presence of sustainable and environmentally benign metal catalyst, FeCl3. This method provides a straightforward approach for the synthesis of N-aryl substituted pyrroles in good yields from easily accessible starting materials such as nitroalkenes, 1,3-dicarbonyl

  摘要描述了在可持续和环境友好的金属催化剂 FeCl3 存在下，高效且操作简单的三组分偶联合成各种 N-芳基取代吡咯。该方法提供了一种直接的方法，用于从易于获得的起始材料（如硝基烯烃、1,3-二羰基化合物和伯芳香胺）以良好的收率合成 N-芳基取代的吡咯。该反应通过 Fe(III) 催化的胺化/迈克尔/环异构化反应的催化序列进行。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Synthesis of Nitroalkenes Involving a Cooperative Catalytic Action of Iron(III) and Piperidine: A One-Pot Synthetic Strategy to 3-Alkylindoles, 2<i>H</i>-Chromenes and<i>N</i>-Arylpyrrole
  作者：Swapnadeep Jalal、Soumen Sarkar、Krishnendu Bera、Sukhendu Maiti、Umasish Jana

  DOI：10.1002/ejoc.201300172

  日期：2013.8

  efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable

  已经开发出一种有效且简单的策略来合成各种取代的硝基烯烃，涉及 FeCl3 和哌啶的协同催化体系。这种双催化协议同时激活亲电试剂和亲核试剂，并在温和的反应条件下工作，因此可以耐受许多敏感的官能团。此外，这种协同催化反应还适用于涉及硝基烯烃的各种一锅反应，如2H-色烯、N-芳基吡咯和与吲哚的迈克尔反应。值得注意的是，这种方法成本低、效率高且环保。
• Iron(III)-Catalyzed Four-Component Coupling Reaction of 1,3-Dicarbonyl Compounds, Amines, Aldehydes, and Nitroalkanes: A Simple and Direct Synthesis of Functionalized Pyrroles
  作者：Sukhendu Maiti、Srijit Biswas、Umasish Jana

  DOI：10.1021/jo902661y

  日期：2010.3.5

  A simple, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles catalyzed by iron(III) salts has been developed. This strategy demonstrated four-component coupling reactions of 1,3-dicarbonyl compounds, amines, aromatic aldehydes, and nitroalkanes without an inert atmosphere. This methodology provides an alternative approach for easy access of highly substituted

  已经开发出一种简单，方便和多组分的偶联策略，用于合成铁（III）盐催化的高度官能化的吡咯。该策略证明了1,3-二羰基化合物，胺，芳族醛和硝基烷的四组分偶联反应无需惰性气氛。这种方法学提供了一种替代方法，可通过一锅串联反应，使用四个简单易用的构建基块，以中等到非常高的收率轻松获得高度取代的吡咯。值得注意的是，与现有方法相比，该方法非常便宜，直接且对环境友好。
• Fe3O4@SiO2—CPTMS—Guanidine—SO3H-catalyzed One-Pot Multicomponent Synthesis of Polysubstituted Pyrrole Derivatives under Solvent-Free Conditions
  作者：H. Rostami、L. Shiri

  DOI：10.1134/s1070428019080207

  日期：2019.8

  A highly efficient procedure for the one-pot synthesis of polysubstituted pyrrole derivatives by the reaction between of aniline derivatives, beta-diketones or beta-ketoesters, and beta-nitrostyrene derivatives in the presence of Fe3O4@SiO2-CPTMS-guanidine-SO3H as a reusable magnetic nanocatalyst is reported. The magnetic nanocatalyst was prepared and fully characterized by FTIR spectroscopy, scanning electron microscopy, energy dispersive X-ray spectroscopy, X-ray diffraction analysis, thermogravimetric analysis, and vibrating sample magnetometry.
• Three-component direct synthesis of substituted pyrroles from easily accessible chemical moieties using hypervalent iodine reagent
  作者：Nikhil C. Jadhav、Prashant B. Jagadhane、Hemlata V. Patile、Vikas N. Telvekar

  DOI：10.1016/j.tetlet.2013.04.014

  日期：2013.6

  A novel and simple three-component system has been developed to synthesize substituted pyrroles from corresponding amines and nitrostyrenes using (diacetoxyiodo)benzene at reflux temperature in ethanol. The good to excellent yields were obtained with different types of functional groups. (C) 2013 Elsevier Ltd. All rights reserved.