Dimethyl 1-benzyl-2-(4-methylphenyl)-5-phenylmethoxypyrrole-3,4-dicarboxylate | 1254332-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Dimethyl 1-benzyl-2-(4-methylphenyl)-5-phenylmethoxypyrrole-3,4-dicarboxylate
• CAS: 1254332-16-5
• 化学式: C₂₉H₂₇NO₅
• 分子量: 469.537
• InChiKey: JJVRVHMHVLDXOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 丁炔二酸二甲酯 在 lithium hexamethyldisilazane 、 三甲基氯硅烷 作用下， 生成 Dimethyl 1-benzyl-2-(4-methylphenyl)-5-phenylmethoxypyrrole-3,4-dicarboxylate
  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