(2R)-2-(5-acetyl-1-methyl-1H-pyrrol-3-yl)-2-hydroxyacetic acid ethyl ester | 1338919-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-(5-acetyl-1-methyl-1H-pyrrol-3-yl)-2-hydroxyacetic acid ethyl ester
• 英文别名: ethyl (2R)-2-(5-acetyl-1-methylpyrrol-3-yl)-2-hydroxyacetate
• CAS: 1338919-37-1
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: TZJUJSCKCXJZBQ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰基-1-甲基吡咯 、 乙醛酸乙酯 在 C₁₂H₂₈O₄Ti*2C₂₀H₁₂Br₂O₂ 作用下， 以 甲苯 为溶剂， 以77%的产率得到(2R)-2-(5-acetyl-1-methyl-1H-pyrrol-3-yl)-2-hydroxyacetic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Friedel–Crafts Reaction of Acylpyrroles with Glyoxylates Catalyzed by BINOL–Ti(IV) Complexes

  摘要：

  We report the first efficient enantioselective Friedel-Crafts hydroxyalkylation of pyrroles having one electron-withdrawing group at the alpha, beta or N-positions with alkyl glyoxylates catalyzed by readily available chiral BINOL-Ti(IV) complexes (1-5 mol %). The reaction regioselectively led to the desired pyrrole-hydroxyacetic acid derivatives with good yields (70-96%) and enantiomeric excesses up to 96%, and is applicable in multigram scale with low loading of the catalyst (1 mol %).

  DOI：

  10.1021/ol202244u

文献信息

• Enantioselective Friedel–Crafts Reaction of Acylpyrroles with Glyoxylates Catalyzed by BINOL–Ti(IV) Complexes
  作者：Jakub Majer、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1021/ol202244u

  日期：2011.11.18

  We report the first efficient enantioselective Friedel-Crafts hydroxyalkylation of pyrroles having one electron-withdrawing group at the alpha, beta or N-positions with alkyl glyoxylates catalyzed by readily available chiral BINOL-Ti(IV) complexes (1-5 mol %). The reaction regioselectively led to the desired pyrrole-hydroxyacetic acid derivatives with good yields (70-96%) and enantiomeric excesses up to 96%, and is applicable in multigram scale with low loading of the catalyst (1 mol %).