diethyl 5-phenyl-1-(p-tolyl)-1H-pyrrole-2,3-dicarboxylate | 1234371-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 5-phenyl-1-(p-tolyl)-1H-pyrrole-2,3-dicarboxylate
• 英文别名: Diethyl 5-phenyl-1-p-tolyl-1h-pyrrole-2,3-di-carboxylate；diethyl 1-(4-methylphenyl)-5-phenylpyrrole-2,3-dicarboxylate
• CAS: 1234371-08-4
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: DDKKNCAFLFCUOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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 、 丁炔二酸二乙酯 在 polyethylene glycol 作用下， 以84%的产率得到diethyl 5-phenyl-1-(p-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

• 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。
• Facile synthesis of polysubstituted 2,3-dihydropyrroles and pyrroles from Mn(OAc)3-promoted oxidative cyclization of alkenes with amines/alkyne esters or enaminone esters
  作者：Ji-Chao Zeng、Hui Xu、Rong-Lu Huang、Fei Yu、Ze Zhang

  DOI：10.1016/j.tetlet.2018.03.025

  日期：2018.4

  A novel oxidative cyclization of alkenes with amines/alkyne esters or enaminone esters can be efficiently promoted by Mn(OAc)3, furnishing a series of polysubstituted 2,3-dihydropyrroles in moderate to excellent isolated yields (75–91%). Afterward addition of a suitable oxidant such as K2S2O8 can furnish efficient synthesis of the corresponding polysubstituted pyrroles in a one-pot pathway.

  Mn（OAc）3可以有效地促进烯烃与胺/炔烃酯或烯胺酯的新型氧化环化反应，从而以中等至优异的分离产率（75-91％）提供一系列多取代的2,3-二氢吡咯。之后加入合适的氧化剂，例如K 2 S 2 O 8，可以在一锅法中有效合成相应的多取代吡咯。
• 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.