dimethyl 5-phenyl-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylate | 1234371-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 5-phenyl-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylate
• 英文别名: dimethyl 5-phenyl-1-p-tolyl-1H-pyrrole-2,3-dicarboxylate；Dimethyl 5-phenyl-1-p-tolyl-1h-pyrrole-2,3-di-carboxylate；dimethyl 1-(4-methylphenyl)-5-phenylpyrrole-2,3-dicarboxylate
• CAS: 1234371-07-3
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: VDXSSISPYWSKQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 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：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 、 2-溴苯乙酮 、 丁炔二酸二甲酯 在 polyethylene glycol 作用下， 以85%的产率得到dimethyl 5-phenyl-1-(4-tolyl)-1H-pyrrole-2,3-dicarboxylate
  参考文献：
  名称：

  聚乙二醇（PEG-400）作为无催化剂条件下一锅合成多取代吡咯的有效且可循环利用的反应介质

  摘要：

  发现聚乙二醇（PEG）是一种便宜的无毒且有效的介质，用于一锅合成高官能化的吡咯。利用该方案，以优异的产率合成了各种吡咯衍生物。PEG的环境可接受性，低成本，高产率和可回收性是该协议的重要特征。

  DOI：

  10.1016/j.tetlet.2011.04.095

文献信息

• Convenient synthesis of polysubstituted pyrroles and symmetrical and unsymmetrical bis-pyrroles catalyzed by H3PW12O40
  作者：Mohammad Soltani、Iraj Mohammadpoor-Baltork、Ahmad R. Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani

  DOI：10.1016/j.crci.2015.11.006

  日期：2016.3

  mild and environmentally-benign protocol for the efficient synthesis of polysubstituted pyrroles via a one-pot three-component reaction of amines, α-bromo ketones and dialkyl acetylenedicarboxylate using H 3 PW 12 O 40 as a recyclable heterogeneous catalyst under solvent-free conditions at room temperature is reported. Importantly, the synthesis of symmetrical and unsymmetrical polysubstituted bis-pyrroles

  摘要 使用 H 3 PW 12 O 40 作为可回收的多相催化剂，在无溶剂条件下，通过胺、α-溴酮和乙炔二羧酸二烷基酯的一锅三组分反应高效合成多取代吡咯的温和且环境友好的方案报告了室温条件。重要的是，对称和不对称多取代双吡咯的合成首次以良好的产量进行，这可以被视为该协议的一个显着特征。
• 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。
• Synthesis of polysubstituted pyrroles in aqueous medium directly from nitro compounds
  作者：L. Madhava Reddy、P. Chandrashekar、A. R. Reddy、C. K. Reddy

  DOI：10.1134/s1070363215010272

  日期：2015.1

  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.
• 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.
• Polyethylene glycol (PEG-400) as an efficient and recyclable reaction medium for one-pot synthesis of polysubstituted pyrroles under catalyst-free conditions
  作者：Lingaiah Nagarapu、Raghu Mallepalli、Lingappa Yeramanchi、Rajashaker Bantu

  DOI：10.1016/j.tetlet.2011.04.095

  日期：2011.6

  Polyethylene glycol (PEG) was found to be an inexpensive non-toxic and effective medium for the one-pot synthesis of highly functionalized pyrroles. Utilizing this protocol various pyrrole derivatives were synthesized in excellent yields. Environmental acceptability, low cost, high yields, and recyclability of the PEG are the important features of this protocol.

  发现聚乙二醇（PEG）是一种便宜的无毒且有效的介质，用于一锅合成高官能化的吡咯。利用该方案，以优异的产率合成了各种吡咯衍生物。PEG的环境可接受性，低成本，高产率和可回收性是该协议的重要特征。