5-(4-chlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 4-ethyl ester | 952019-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 4-ethyl ester
• 英文别名: 2-(4-Chlorophenyl)-4-ethoxycarbonyl-1-(4-methoxyphenyl)-5-methylpyrrole-3-carboxylic acid
• CAS: 952019-85-1
• 化学式: C₂₂H₂₀ClNO₅
• 分子量: 413.858
• InChiKey: AYYMHUJUKSQRDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 4-ethyl ester 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-6-methyl-2-piperidin-1-yl-5H-pyrrole-[3,4-c]pyrrole-1,3-dione
  参考文献：
  名称：

  Regioselective Synthesis of Highly Aryl‐Substituted Pyrrole Carboxylates as Useful Medicinal Chemistry Leads

  摘要：

  The regioselective syntheses of two pharmaceutically relevant pyrrole scaffolds are described. A synthetic route for the preparation of differentially substituted pyrrole-3,4-dicarboxylates is presented and exemplified. This route circumvents some of the problems and limitations associated with previous butynedioic diester condensations and 1,3-dipolar cycloaddition reactions. A route to the related 4,5-diarylpyrrole2-carboxylic acid scaffold is also presented. Both routes allow for the regiocontrolled preparation of highly substituted pyrrole pharmacophore cores.

  DOI：

  10.1080/00397910701481237
• 作为产物：
  描述：

  4-氯-N-甲氧基-N-甲基乙酰胺 在 sodium ethanolate 、 溶剂黄146 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 38.42h， 生成 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 4-ethyl ester
  参考文献：
  名称：

  Regioselective Synthesis of Highly Aryl‐Substituted Pyrrole Carboxylates as Useful Medicinal Chemistry Leads

  摘要：

  The regioselective syntheses of two pharmaceutically relevant pyrrole scaffolds are described. A synthetic route for the preparation of differentially substituted pyrrole-3,4-dicarboxylates is presented and exemplified. This route circumvents some of the problems and limitations associated with previous butynedioic diester condensations and 1,3-dipolar cycloaddition reactions. A route to the related 4,5-diarylpyrrole2-carboxylic acid scaffold is also presented. Both routes allow for the regiocontrolled preparation of highly substituted pyrrole pharmacophore cores.

  DOI：

  10.1080/00397910701481237

文献信息

• Regioselective Synthesis of Highly Aryl‐Substituted Pyrrole Carboxylates as Useful Medicinal Chemistry Leads
  作者：Ulhas Bhatt、Bryan C. Duffy、Peter R. Guzzo、Leifeng Cheng、Thomas Elebring

  DOI：10.1080/00397910701481237

  日期：2007.8

  The regioselective syntheses of two pharmaceutically relevant pyrrole scaffolds are described. A synthetic route for the preparation of differentially substituted pyrrole-3,4-dicarboxylates is presented and exemplified. This route circumvents some of the problems and limitations associated with previous butynedioic diester condensations and 1,3-dipolar cycloaddition reactions. A route to the related 4,5-diarylpyrrole2-carboxylic acid scaffold is also presented. Both routes allow for the regiocontrolled preparation of highly substituted pyrrole pharmacophore cores.