4-ethyl 2,3-dimethyl 1-benzyl-5-methyl-1H-pyrrole-2,3,4-tricarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-ethyl 2,3-dimethyl 1-benzyl-5-methyl-1H-pyrrole-2,3,4-tricarboxylate
• 英文别名: 4-ethyl-2,3-dimethyl 1-benzyl-5-methyl-1H-pyrrole-2,3,4-tricarboxylate；1-benzyl-3-ethoxycarbonyl-4,5-dimethoxycarbonyl-2-methylpyrrole；4-Ethyl 2,3-dimethyl 1-benzyl-5-methyl-1 h-pyrrole-2,3,4-tricarboxylate；4-O-ethyl 2-O,3-O-dimethyl 1-benzyl-5-methylpyrrole-2,3,4-tricarboxylate
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: AQFDAQIBMSVALX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 4-ethyl 2,3-dimethyl 1-benzyl-5-methyl-1H-pyrrole-2,3,4-tricarboxylate
  参考文献：
  名称：

  An efficient and convenient synthesis of pentasubstituted pyrroles from alkyl acetoacetates, dialkyl acetylenedicarboxylates, and amines

  摘要：

  A simple and efficient synthesis of pentasubstituted pyrroles has been developed using a one-pot, two-step reaction. The synthesis of a series of 4-hydroxypenta-1,3-diene-tricarboxylates from alkyl acetoacetates and dialkyl acetylenedicarboxylates in the presence of K2CO3, followed by cyclization with amines, gave the corresponding pyrroles in excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.025

文献信息

• A Novel Assembly of Substituted Pyrroles by Acid-Catalyzed Sequential Three-Component Reaction of Amines, Alkynoates, and 1,2-Diaza-1,3-dienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Fabio Mantellini、Giada Moscatelli、Stefania Santeusanio

  DOI：10.1002/adsc.201100094

  日期：2011.6

  A novel protocol for the assembly of polysubstituted pyrroles has been developed through the acid‐catalyzed, sequential three‐component reaction of primary aliphatic amines, alkynoates and 1,2‐diaza‐1,3‐dienes (DDs). This methodology proceeds with complete chemo‐/regioselectivity involving first formation of an enamino ester intermediate, in situ Michael addition with azo‐ene compounds and subsequent

  通过伯脂肪族胺，炔酸和1,2-二氮杂-1,3-二烯（DDs）的酸催化顺序三组分反应，开发了一种多取代吡咯组装的新方案。该方法具有完全的化学/区域选择性，包​​括首先形成烯氨基酯中间体，与偶氮烯化合物在原位迈克尔加成，然后进行分子内闭环。
• Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods
  作者：Maryam Sabbaghan、Haleh Sanaeishoar、Azam Ghalaei、Pegah Sofalgar

  DOI：10.1007/s13738-015-0697-6

  日期：2015.12

  An efficient zinc oxide nanorod-catalyzed one-pot strategy has been developed for the synthesis of polysubstituted pyrroles in very good yields. The present approach provides a three-component reaction between primary alkylamines, dialkyl acetylenedicarboxylates, and 2-chloro-1,3-dicarbonyl compounds with several advantages such as short reaction time, high yields, solvent free, and little catalyst loading. After reaction course, ZnO nanorods can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence eco-friendly.

  我们开发了一种高效的氧化锌纳米棒催化单锅策略，用于合成多取代吡咯，收率非常高。本方法提供了伯烷基胺、乙炔二羧酸二烷基酯和 2-氯-1,3-二羰基化合物之间的三组分反应，具有反应时间短、产率高、无溶剂和催化剂负载少等优点。反应过程结束后，氧化锌纳米棒可回收再利用，活性不会明显降低，因此该工艺具有成本效益，而且环保。
• Fe3O4 nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 1H-indole and 1H-pyrrole derivatives
  作者：Seyyed Ebrahim Babaei、Zinatossadat Hossaini、Reza Ramezani Besheli、Vahid Tavakkoli

  DOI：10.1007/s10593-016-1880-0

  日期：2016.5

  Magnetic Fe3O4 nanoparticles as a heterogeneous catalyst were found to be efficient for the synthesis of a series of pyrrole and indole derivatives using three-component reactions of primary amines, 1,3-dicarbonyl compounds, and activated acetylenic compounds under solvent-free conditions at room temperature. The present protocol offers the advantages of clean reaction, short reaction time, high yield

  发现磁性Fe 3 O 4纳米颗粒作为非均相催化剂可有效地在无溶剂条件下使用伯胺，1,3-二羰基化合物和活化炔属化合物的三组分反应合成一系列吡咯和吲哚衍生物在室温条件下。本方案提供了清洁反应，短反应时间，高收率，易于纯化和催化剂负担能力的优点。
• Oxidative free radical reactions of enamino esters
  作者：Che-Ping Chuang、Yi-Lung Wu

  DOI：10.1016/j.tet.2003.12.035

  日期：2004.2

  produced by the cerium(IV) ammonium nitrate (CAN) oxidation of β-dicarbonyl compounds undergo efficient addition to the C–C double bond of enamino esters. This CAN mediated free radical reaction between enamino esters and β-dicarbonyl compounds provides a novel method for the synthesis of highly substituted pyrroles. The direct CAN oxidation of β-enaminocinnamates gave the dimerization products effectively

  描述了烯氨基酯的氧化自由基反应。β-二羰基化合物的硝酸铈（IV）硝酸铈铵（CAN）氧化产生的亲电子碳中心基团经过有效地添加到烯氨基酯的C-C双键中。烯胺酸酯和β-二羰基化合物之间的CAN介导的自由基反应为合成高度取代的吡咯提供了一种新颖的方法。β-烯胺肉桂酸酯的直接CAN氧化有效地产生了二聚产物。
• An efficient and convenient synthesis of pentasubstituted pyrroles from alkyl acetoacetates, dialkyl acetylenedicarboxylates, and amines
  作者：Hossein Mehrabi、Mohammad Anary-Abbasinejad、Fatemeh Mirhashemi

  DOI：10.1016/j.tetlet.2014.06.025

  日期：2014.7

  A simple and efficient synthesis of pentasubstituted pyrroles has been developed using a one-pot, two-step reaction. The synthesis of a series of 4-hydroxypenta-1,3-diene-tricarboxylates from alkyl acetoacetates and dialkyl acetylenedicarboxylates in the presence of K2CO3, followed by cyclization with amines, gave the corresponding pyrroles in excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.