1-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl]-ethanone | 1208334-46-6

• 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-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl]-ethanone
• 英文别名: 1-(4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl)ethanone；1-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl]ethanone；1-[4-(4-Chlorophenyl)-1-(4-methoxyphenyl)-2-methylpyrrol-3-yl]ethanone
• CAS: 1208334-46-6
• 化学式: C₂₀H₁₈ClNO₂
• 分子量: 339.821
• InChiKey: JHSWQBNKAROTAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl]-ethanone 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 71.0h， 以46%的产率得到C₂₀H₁₇Cl₂NO₂
  参考文献：
  名称：

  FeCl3介导二氢吡咯并[2,1-a]异喹啉的二聚和四取代吡咯的氯化。

  摘要：

  我们已经开发了通过FeCl3介导的氧化均质偶合的二氢吡咯并[2,1-a]异喹啉的温和直接二聚。以可接受的优异产率（高达> 99％）获得了一系列二聚二氢吡咯并异喹啉衍生物。尝试将该二聚体系扩展至二聚吡咯的合成失败，并且在大多数情况下获得了氯化产物而不是二聚吡咯。

  DOI：

  10.1039/c9ob02607j
• 作为产物：
  描述：

  1-(4-氯苯基)-2-硝基乙烯 、 甲氧苯胺 、 乙酰丙酮 在 iron(III) chloride 作用下， 以 硝基甲烷 为溶剂， 反应 10.0h， 以71%的产率得到1-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl]-ethanone
  参考文献：
  名称：

  氯化铁催化三组分偶联合成多取代的N-芳基吡咯

  摘要：

  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

  DOI：

  10.1080/00397911.2011.650273

文献信息

• The acidic ionic liquid [BSO₃HMIm]HSO₄: a novel and efficient catalyst for one-pot, three-component syntheses of substituted pyrroles
  作者：Yuan Luo、Bao-Qiang Zhang、Yan-Hong He、Zhi Guan

  DOI：10.1515/znb-2014-0108

  日期：2015.1.1

  was used as an efficient catalyst for the synthesis of a variety of pyrrole derivatives via a one-pot, three-component condensation of amines, nitroolefins, and 1,3-dicarbonyl compounds. Good to excellent yields of 72–96% were obtained under reflux in ethanol. The catalyst could easily be recovered and recycled up to six times, resulting in good yields without prolonging the reaction time. This method

  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。
• An efficient synthesis of highly substituted functionalized pyrroles via a four-component coupling reaction catalyzed by Fe(III)-Schiff base/SBA-15
  作者：Ghasem Rezanejade Bardajee、Aseyeh Ghaedi、Hamideh Hazrati、Farnaz Jafarpour

  DOI：10.1080/24701556.2020.1744650

  日期：2020.12.1

  Abstract An environmentally friendly, straightforward, and cheap synthesis of highly substituted functionalized pyrrole derivatives via one pot four-component reactions of 1,3-dicarbonyl compounds, amines, aromatic aldehydes, and nitroalkanes have been developed. This methodology provides desired pyrroles in good-to-excellent yields in the presence of Fe (III)-Schiff base/SBA-15 as a heterogeneous

  摘要 通过1，3-二羰基化合物，胺，芳族醛和硝基烷的一锅四组分反应，已经开发了一种环境友好，直接且廉价的高取代官能化吡咯衍生物的合成方法。该方法在Fe（III）-席夫碱/ SBA-15作为非均相催化剂存在下，以良好至优异的产率提供了所需的吡咯。
• 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。
• Modular CeCl3·7H2O-catalyzed multi-component synthesis of 1,2,3,4-tetrasubstituted pyrroles under microwave irradiation and their further trichloroisocyanuric acid-mediated conversion into 5-sulfenylpyrrole derivatives
  作者：Claudio C. Silveira、Samuel R. Mendes、Guilherme M. Martins、Sheila C. Schlösser、Teodoro S. Kaufman

  DOI：10.1016/j.tet.2013.08.035

  日期：2013.10

  A modular, multicomponent synthesis of 1,2,3,4-tetrasubstituted pyrroles promoted by the inexpensive CeCl3 center dot 7H(2)O, is reported. The reaction was carried out under microwave irradiation, affording good yields of products in short time. Scope and limitations were explored and a plausible reaction mechanism is discussed. The resulting heterocycles were smoothly and efficiently converted into their corresponding 5-arylsulfenyl derivatives by reaction with diaryl disulfides and trichloroisocyanuric acid in EtOAc. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.