4-ethyl 2,3-dimethyl 1-ethyl-5-methyl-1H-pyrrole-2,3,4-tricarboxylate | 1620102-96-6

• 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-ethyl-5-methyl-1H-pyrrole-2,3,4-tricarboxylate
• 英文别名: 4-Ethyl 2,3-dimethyl 1-ethyl-5-methyl-1 h-pyrrole-2,3,4-tricarboxylate；4-O-ethyl 2-O,3-O-dimethyl 1-ethyl-5-methylpyrrole-2,3,4-tricarboxylate
• CAS: 1620102-96-6
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: KSBDRJYOELKIOU-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C
• 沸点：
  357.1±37.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-ethyl-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

• 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。