triethyl 1-(4-methylbenzyl)-5-methyl-1H-pyrrole-2,3,4-tricarboxylate | 1620102-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: triethyl 1-(4-methylbenzyl)-5-methyl-1H-pyrrole-2,3,4-tricarboxylate
• CAS: 1620102-93-3
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: BSWQMNOAVPWMMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.83
• 氢给体数：
  0.0
• 氢受体数：
  7.0

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 triethyl 1-(4-methylbenzyl)-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

• TBAI‐Catalyzed, TBHP‐Mediated Modular Three‐Component Cascade Towards Highly Functionalized Pyrrole via [3+2] Annulation
  作者：Karthiyayini Gnanaoli、Deepan Babu Rajkumar、Keerthana Gopal、B. Saritha、C. Uma Maheswari

  DOI：10.1002/ejoc.202400197

  日期：2024.5.27

  A simple, one-pot sequential synthesis of highly substituted pyrrole under the metal-free condition catalyzed by TBAI/TBHP was demonstrated. β-Enaminone generated in situ from β-ketoesters and primary amines reacts with electron-deficient alkynes to synthesize penta-substituted pyrroles.

  演示了在 TBAI/TBHP 催化下，在无金属条件下简单、一锅连续合成高取代吡咯的方法。由β-酮酯和伯胺原位生成的β-烯胺酮与缺电子炔烃反应合成五取代吡咯。