2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl ester | 952019-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl ester
• 英文别名: 5-(2,4-Dichlorophenyl)-1-(4-methoxyphenyl)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl]pyrrole-3-carboxylic acid
• CAS: 952019-79-3
• 化学式: C₂₄H₂₃Cl₂NO₅
• 分子量: 476.356
• InChiKey: PDCIJIVUBPNNGB-UHFFFAOYSA-N

物化性质

• 沸点：
  622.0±55.0 °C(Predicted)
• 密度：
  1.29±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：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3,4-dicarboxylic acid 3-tert-butyl ester 、 1-氨基哌啶 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45%的产率得到2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-4-(piperidin-1-ylcarbamoyl)-1H-pyrrole-3-carboxylic 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
• 作为产物：
  描述：

  N-甲氧基-n-甲基-2,4-二氯苯甲酰胺 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 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-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