2-acetyl-3-(4-chlorobenzoyl)succinic acid 4-tert-butyl ester 1-ethyl ester | 952019-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-3-(4-chlorobenzoyl)succinic acid 4-tert-butyl ester 1-ethyl ester
• 英文别名: 4-O-tert-butyl 1-O-ethyl 2-acetyl-3-(4-chlorobenzoyl)butanedioate
• CAS: 952019-72-6
• 化学式: C₁₉H₂₃ClO₆
• 分子量: 382.841
• InChiKey: XWJRIJXVJDTHTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-(4-chlorobenzoyl)succinic acid 4-tert-butyl ester 1-ethyl ester 在 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 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
• 作为产物：
  描述：

  4-氯-N-甲氧基-N-甲基乙酰胺 在 sodium ethanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 11.42h， 生成 2-acetyl-3-(4-chlorobenzoyl)succinic acid 4-tert-butyl ester 1-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.