Methyl 1-benzyl-4-methyl-2,5-bis(4-methylphenyl)pyrrole-3-carboxylate | 1254332-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Methyl 1-benzyl-4-methyl-2,5-bis(4-methylphenyl)pyrrole-3-carboxylate
• 英文别名: methyl 1-benzyl-4-methyl-2,5-bis(4-methylphenyl)pyrrole-3-carboxylate
• CAS: 1254332-21-2
• 化学式: C₂₈H₂₇NO₂
• 分子量: 409.528
• InChiKey: AMJZGFLLZNKXSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 2-丁炔酸甲酯 在 lithium hexamethyldisilazane 、 三甲基氯硅烷 作用下， 以31%的产率得到Methyl 1-benzyl-4-methyl-2,5-bis(4-methylphenyl)pyrrole-3-carboxylate
  参考文献：
  名称：

  Horner−Wadsworth−Emmons Reagents as Azomethine Ylide Analogues: Pyrrole Synthesis via (3 + 2) Cycloaddition

  摘要：

  Amido-substituted Horner-Wadsworth-Emmons reagents can serve as precursors to 1,3-dipoles for use in cycloaddition. These compounds are assembled in one pot via the TMSOTf-catalyzed Arbuzov reaction of imines, acid chlorides, and phosphites. The coupling of this synthesis with alkyne cycloaddition provides a three-component synthesis of pyrroles. The dipoles can be prepared with a diverse range of imines and acid chlorides, and (3 + 2) cycloaddition with unsymmetrical alkynes is highly regiospecific, providing a modular approach to form substituted pyrroles.

  DOI：

  10.1021/ol102075y

文献信息

• Horner−Wadsworth−Emmons Reagents as Azomethine Ylide Analogues: Pyrrole Synthesis via (3 + 2) Cycloaddition
  作者：Marie S. T. Morin、Daniel J. St-Cyr、Bruce A. Arndtsen

  DOI：10.1021/ol102075y

  日期：2010.11.5

  Amido-substituted Horner-Wadsworth-Emmons reagents can serve as precursors to 1,3-dipoles for use in cycloaddition. These compounds are assembled in one pot via the TMSOTf-catalyzed Arbuzov reaction of imines, acid chlorides, and phosphites. The coupling of this synthesis with alkyne cycloaddition provides a three-component synthesis of pyrroles. The dipoles can be prepared with a diverse range of imines and acid chlorides, and (3 + 2) cycloaddition with unsymmetrical alkynes is highly regiospecific, providing a modular approach to form substituted pyrroles.