5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-hydroxy-5-oxo-pentanoic acid methyl ester | 952019-90-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-hydroxy-5-oxo-pentanoic acid methyl ester
• 英文别名: methyl (2R)-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-hydroxy-5-oxopentanoate
• CAS: 952019-90-8
• 化学式: C₁₈H₁₅Cl₃O₄
• 分子量: 401.674
• InChiKey: AVQLWICPPZBGDA-BZSJEYESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-hydroxy-5-oxo-pentanoic acid methyl ester 在 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid methyl 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 hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.25h， 生成 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-hydroxy-5-oxo-pentanoic acid methyl 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.