5-(4-nitrophenyl)-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylic acid dimethyl ester | 1172616-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-nitrophenyl)-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 1-(4-methylphenyl)-5-(4-nitrophenyl)-pyrrole-2,3-dicarboxylate；dimethyl 5-(4-nitrophenyl)-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylate；dimethyl 5-(4-nitrophenyl)-1-p-tolyl-1H-pyrrole-2,3-dicarboxylate；dimethyl 1-(4-methylphenyl)-5-(4-nitrophenyl)pyrrole-2,3-dicarboxylate
• CAS: 1172616-51-1
• 化学式: C₂₁H₁₈N₂O₆
• 分子量: 394.384
• InChiKey: ZGOSAVRSLROBRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基甲苯 、 2-溴-4'-硝基苯乙酮 、 丁炔二酸二甲酯 在 盐酸 、 indium 作用下， 以 水 为溶剂， 反应 16.0h， 以80%的产率得到5-(4-nitrophenyl)-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of polysubstituted pyrroles in aqueous medium directly from nitro compounds

  摘要：

  A novel approach for the synthesis of polysubstituted pyrroles has been followed through multicomponent reaction of nitro compounds, phenacyl bromide or its derivatives and dialkyl acetylene dicarboxylates using indium in dilute aqueous HCl at room temperature. The products are formed in high yields (75-87%) in 10-16 h.

  DOI：

  10.1134/s1070363215010272

文献信息

• Ionic Liquid Promoted Multicomponent Reaction: A Good Strategy for the Eco-Compatible Synthesis of Functionalized Pyrroles
  作者：I. R. Siddiqui、Devesh Kumar、Shayna Shamim

  DOI：10.1002/jhet.1085

  日期：2013.2

  reusable, alternative, and effective reaction media for multicomponent synthesis of highly functionalized pyrroles. Generality of the procedure was established by synthesizing various pyrroles from wide range of aromatic/aliphatic amine, phenacyl bromide, and electrophilic alkynes by utilizing this protocol without any acid or metal catalyst. Ecocompatibility, short reaction time, excellent yield, recyclability

  发现特定于任务的[bmim] BF 4是可重复使用的，替代的且有效的反应介质，可用于高度官能化吡咯的多组分合成。该方法的一般性是通过从各种芳香族/脂肪族胺中合成各种吡咯而建立的，苯甲酰溴和亲电炔烃，利用该方案无需任何酸或金属催化剂。生态相容性，短的反应时间，优异的产率，[bmim] BF 4的可回收性，低成本，易于后处理和温和的反应条件是该方法在可持续和绿色化学方面的其他优点。
• An Efficient New Method for the Synthesis of Polysubstituted Pyrroles¹
  作者：Biswanath Das、Gandolla Reddy、Penagaluri Balasubramanyam、Boyapati Veeranjaneyulu

  DOI：10.1055/s-0029-1218703

  日期：2010.5

  The three-component reactions of phenacyl bromide or its derivatives, amine, and dialkyl acetylenedicarboxylate in the presence of iron(III) chloride as a catalyst at room temperature afforded polysubstituted pyrroles in high yields. polysubstituted pyrroles - three-component reaction - iron(III) chloride Part 283 in the series ‘Studies on Novel Synthetic Methodologies’.

  在室温下，在氯化铁（III）作为催化剂存在下，苯甲酰溴或其衍生物，胺和乙酰二羧酸二烷基酯的三组分反应在高产率下提供了多取代的吡咯。 多取代的吡咯-三组分反应-氯化铁（III） 系列“新型合成方法研究”的第283部分。
• A Novel Approach to the Synthesis of Highly Functionalized Pyrroles
  作者：Mohammad Anary-Abbasinejad、Khadije Charkhati、Hossein Anaraki-Ardakani

  DOI：10.1055/s-0028-1088224

  日期：2009.4

  A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives by a three-component reaction between dialkyl acetylenedicarboxylates, aromatic amines, triphenylphosphine, and arylglyoxals is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded high yields of products.

  描述了通过二烷基乙炔二羧酸酯、芳香胺、三苯基膦和芳基乙二醛之间的三组分反应合成多取代吡咯衍生物的一种新的、有效的一锅法。该反应在室温和中性条件下在二氯甲烷中进行，并提供高产率的产物。
• Novel and efficient supramolecular synthesis of pyrroles in the presence of β-cyclodextrin in water
  作者：K. Ramesh、K. Karnakar、G. Satish、Y.V.D. Nageswar

  DOI：10.1016/j.cclet.2012.11.005

  日期：2012.12

  A simple and efficient synthesis of highly substituted pyrroles was achieved in water medium via multi-component strategy, using amine, DMAD/DEAD as well as phenacyl bromide catalyzed by beta-CD. Utilizing this protocol various pyrrole derivatives were synthesized in good to excellent yields. (C) 2012 Y.V.D. Nageswar. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.