(1'S,2'R,5'S)-menthyl 1-acetyl-2-oxoimidazolidine-4(S)-carboxylate | 872619-08-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1'S,2'R,5'S)-menthyl 1-acetyl-2-oxoimidazolidine-4(S)-carboxylate
• 英文别名: [(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (4S)-1-acetyl-2-oxoimidazolidine-4-carboxylate
• CAS: 872619-08-4
• 化学式: C₁₆H₂₆N₂O₄
• 分子量: 310.393
• InChiKey: NTIDMPKHIJRURB-GHYVTOPFSA-N

物化性质

• 熔点：
  77-78 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'S,2'R,5'S)-menthyl 1-acetyl-2-oxoimidazolidine-4(S)-carboxylate 、 dirhodium tetraacetate 、 乙腈 以 氯苯 为溶剂， 以46%的产率得到dirhodium(II) tetrakis[(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 钯 吡啶 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 138.0h， 生成 (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