(2R)-2-[1-(benzyloxycarbonyl)-1H-pyrrol-2-yl]-2-hydroxyacetic acid n-butyl ester | 1338919-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-[1-(benzyloxycarbonyl)-1H-pyrrol-2-yl]-2-hydroxyacetic acid n-butyl ester
• 英文别名: benzyl 2-[(1R)-2-butoxy-1-hydroxy-2-oxoethyl]pyrrole-1-carboxylate
• CAS: 1338919-52-0
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: PFSROLWQMLTKRI-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dibutyl tartrate 在 titanium(IV) isopropylate 、 sodium periodate 、 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 (2S)-2-[1-(benzyloxycarbonyl)-1H-pyrrol-2-yl]-2-hydroxyacetic acid n-butyl ester 、 (2R)-2-[1-(benzyloxycarbonyl)-1H-pyrrol-2-yl]-2-hydroxyacetic acid n-butyl 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 %).