(2S,5S)-5-Benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one | 1428736-46-2

• 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: (2S,5S)-5-Benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one
• 英文别名: (2S,5S)-5-benzyl-2,5-dimethyl-2-pyridin-2-ylimidazolidin-4-one
• CAS: 1428736-46-2
• 化学式: C₁₇H₁₉N₃O
• 分子量: 281.357
• InChiKey: CMXSFGCWABXQMW-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  alpha-甲基-DL-苯丙氨酸 在 cinchonidine 、 氯甲酸乙酯 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 邻二氯苯 为溶剂， 反应 178.12h， 生成 (2R,5S)-5-benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 、 (2S,5S)-5-Benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one
  参考文献：
  名称：

  Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-one ligands

  摘要：

  Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (alpha-methylDOPA and alpha-methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectiyity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.007

文献信息

• Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-one ligands
  作者：Pavel Drabina、Sergej Karel、Illia Panov、Miloš Sedlák

  DOI：10.1016/j.tetasy.2013.02.007

  日期：2013.3

  Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (alpha-methylDOPA and alpha-methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectiyity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention. (C) 2013 Elsevier Ltd. All rights reserved.