(1'S,2'R,5'S)-menthyl 1-acetyl-3-benzyloxycarbonyl-2-oxoimidazolidine-4(S)-carboxylate | 872619-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1'S,2'R,5'S)-menthyl 1-acetyl-3-benzyloxycarbonyl-2-oxoimidazolidine-4(S)-carboxylate
• CAS: 872619-07-3
• 化学式: C₂₄H₃₂N₂O₆
• 分子量: 444.528
• InChiKey: HMWFEYSIYDTQRC-CZGNIMDHSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  538.6±60.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1'S,2'R,5'S)-menthyl 1-acetyl-3-benzyloxycarbonyl-2-oxoimidazolidine-4(S)-carboxylate 在 钯 氢气 作用下， 以 乙酸乙酯 为溶剂， 以79%的产率得到(1'S,2'R,5'S)-menthyl 1-acetyl-2-oxoimidazolidine-4(S)-carboxylate
  参考文献：
  名称：

  Stereoselectivity in metal carbene and Lewis acid-catalyzed reactions from diastereomeric dirhodium(II) carboxamidates: Menthyl N-acetyl-2-oxoimidazolidine-4(S)-carboxylates

  摘要：

  The influence of a chiral menthyl group as the pendant ester substituent on the N-acetyl-2-oxoimidazolidine-4S-carboxylate ligands in chiral dirhodium(II) imidazolidinone catalysts has been examined. Significant match/mismatch influences are evident in the observed stereocontrol for carbon-hydrogen insertion reactions with diazoacetates, but these effects are minimal in cyclopropanation reactions. Steric restrictions prevent effective enantiocontrol in hetero-Diels-Alder reactions using these menthyl-substituted catalysts. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.05.032
• 作为产物：
  描述：

  D-薄荷醇 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 138.0h， 生成 (1'S,2'R,5'S)-menthyl 1-acetyl-3-benzyloxycarbonyl-2-oxoimidazolidine-4(S)-carboxylate
  参考文献：
  名称：

  Stereoselectivity in metal carbene and Lewis acid-catalyzed reactions from diastereomeric dirhodium(II) carboxamidates: Menthyl N-acetyl-2-oxoimidazolidine-4(S)-carboxylates

  摘要：

  The influence of a chiral menthyl group as the pendant ester substituent on the N-acetyl-2-oxoimidazolidine-4S-carboxylate ligands in chiral dirhodium(II) imidazolidinone catalysts has been examined. Significant match/mismatch influences are evident in the observed stereocontrol for carbon-hydrogen insertion reactions with diazoacetates, but these effects are minimal in cyclopropanation reactions. Steric restrictions prevent effective enantiocontrol in hetero-Diels-Alder reactions using these menthyl-substituted catalysts. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.05.032