2-(5-苯甲酰基-1H-吡咯-2-基)乙酸乙酯 | 141054-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(5-苯甲酰基-1H-吡咯-2-基)乙酸乙酯
• 英文名称: ethyl 5-benzoylpyrrol-2-ylacetate
• 英文别名: 1H-Pyrrole-2-acetic acid, 5-benzoyl-, ethyl ester；ethyl 2-(5-benzoyl-1H-pyrrol-2-yl)acetate
• CAS: 141054-41-3
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: RHJUDCIVQIJYHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  402.2±35.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-苯甲酰基-1H-吡咯-2-基)乙酸乙酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以79%的产率得到酮咯酸杂质43
  参考文献：
  名称：

  The AlCL₃Catalyzed Benzoylation of Ethyl Pyrrole-2-Acetate: An Unusual 6-Substitution

  摘要：

  In this study, synthetic methodologies have been developed which are potentially useful in preparing 4- and 5-aroylpyrrole-2-acetic acids bearing no alkyl substituents on the heterocyclic nitrogen. These compounds are structurally related to a class of NSAIDs.

  DOI：

  10.1080/00397919208019277
• 作为产物：
  描述：

  2-苯甲酰基吡咯 、 2-((乙氧基碳硫代)硫代)乙酸乙酯 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以86%的产率得到2-(5-苯甲酰基-1H-吡咯-2-基)乙酸乙酯
  参考文献：
  名称：

  Efficient, intermolecular, oxidative radical alkylation of heteroaromatic systems under “tin-free” conditions

  摘要：

  本文描述了一种新颖且高效的自由基烷基化方法，适用于多种杂环体系，包括吡咯、吲哚、呋喃和噻吩，采用基于黄原酯的自由基化学。该方法可以快速获取各种非甾体抗炎药。

  DOI：

  10.1039/b306966d

文献信息

• Pyrrole-2,3-quinodimethane analogues in the synthesis of indoles. Part 2.1 Synthesis and diels-alder reactions of 1,6-dihydropyrano[4,3-b]pyrrol-6(1H)-ones
  作者：John F.P. Andrews、P.Mark Jackson、Christopher J. Moody

  DOI：10.1016/s0040-4020(01)87212-4

  日期：1993.8

  The pyrano[4,3-b]pyrrol-6-ones 7-9, 12 and 13 are stable cyclic analogues of pyrole-2,3-quinodimethane, and undergo Diels-Alder reaction with a range of alkynes to give, after loss of carbon dioxide, indoles.

  的吡喃并[4,3- b ]吡咯-6-酮7-9，12和13是吡咯-2,3-醌二甲烷的稳定环状类似物，并经历与一系列炔烃，得到Diels-Alder反应，丢失后二氧化碳，吲哚。
• Et3B-Mediated radical alkylation of pyrroles and indoles
  作者：Miguel A. Guerrero、Luis D. Miranda

  DOI：10.1016/j.tetlet.2006.02.052

  日期：2006.4

  An efficient Et3B-mediated oxidative radical substitution of substituted pyrroles and indoles using xanthate based radical chemistry in the presence of iron(II) sulfate is described. Unsubstituted indole gave only low yield or failed in the process. 2-Cyano-furan and 2-benzoylthiophene did not afford the corresponding alkylated products under these conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• Efficient, intermolecular, oxidative radical alkylation of heteroaromatic systems under “tin-free” conditions
  作者：Yazmin M. Osornio、Raymundo Cruz-Almanza、Vicente Jiménez-Montaño、Luis D. Miranda

  DOI：10.1039/b306966d

  日期：——

  Novel and efficient radical alkylation of several heterocyclic systems including pyrroles, indoles, furan and thiophenes is described using xanthate based radical chemistry. The present methodology could be used to provide rapid access to various nonsteroidal antiinflammatory drugs.

  本文描述了一种新颖且高效的自由基烷基化方法，适用于多种杂环体系，包括吡咯、吲哚、呋喃和噻吩，采用基于黄原酯的自由基化学。该方法可以快速获取各种非甾体抗炎药。
• The AlCL₃Catalyzed Benzoylation of Ethyl Pyrrole-2-Acetate: An Unusual 6-Substitution
  作者：Elena Alexandrou、Eleni Rekka、Vassilis J. Demopoulos

  DOI：10.1080/00397919208019277

  日期：1992.3

  In this study, synthetic methodologies have been developed which are potentially useful in preparing 4- and 5-aroylpyrrole-2-acetic acids bearing no alkyl substituents on the heterocyclic nitrogen. These compounds are structurally related to a class of NSAIDs.