1,2-bis(4-chlorophenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl ester | 952019-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,2-bis(4-chlorophenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl ester
• 英文别名: 1,5-Bis(4-chlorophenyl)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl]pyrrole-3-carboxylic acid
• CAS: 952019-80-6
• 化学式: C₂₃H₂₁Cl₂NO₄
• 分子量: 446.33
• InChiKey: WRONBLOGJCREHH-UHFFFAOYSA-N

物化性质

• 沸点：
  607.3±55.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-chlorophenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl ester 、 4-(三氟甲基)苯肼 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以65%的产率得到1-(2-chlorophenyl)-2-(4-chlorophenyl)-5-methyl-4-[N'-(4-trifluoromethylphenyl)-hydrazinocarbonyl]-1H-pyrrole-3-carboxylic acid tert-butyl 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
• 作为产物：
  描述：

  4-氯-N-甲氧基-N-甲基乙酰胺 在 sodium hydroxide 、 sodium ethanolate 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 35.42h， 生成 1,2-bis(4-chlorophenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl 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.