(1S)-N-[(1S)-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]ethyl]-1-phenylethanamine | 1233132-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S)-N-[(1S)-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]ethyl]-1-phenylethanamine
• CAS: 1233132-51-8
• 化学式: C₂₈H₃₀N₂O₂
• 分子量: 426.558
• InChiKey: CPIYANOAWBQOJR-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-N-[(1S)-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]ethyl]-1-phenylethanamine 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 50.0 ℃ 、377.13 kPa 条件下， 以293 g的产率得到(S)-1-(4-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)phenyl)ethanamine
  参考文献：
  名称：

  Highly Diastereoselective Hydrogenation of Imines by a Bimetallic Pd−Cu Heterogeneous Catalyst

  摘要：

  An efficient and practical heterogeneous bimetallic Pd-Cu/C catalyst was identified as an alternative to Raney nickel for the highly diastereoselective hydrogenation of imines prepared from prochiral ketones and alpha-phenylethylamines. Chiral amines were obtained with diastereomeric excess (de) up to 94% using Pd-Cu/C, while conventional Pd-C catalysts afforded only 72% de. Optimization showed that a robust process required a palladium/copper ratio of 4:1. Evidence for the influence of catalyst pretreatment which may change the structure of the catalyst and/or metal oxidation states on the selectivity of the reaction is discussed. The bimetallic catalyst system provided consistent results on scale and performed reliably on a variety of substrates.

  DOI：

  10.1021/op1001325
• 作为产物：
  描述：

  1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-N-[(1S)-1-phenylethyl]ethanimine 在 5% palladium-copper on carbon 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 25.0 ℃ 、273.7 kPa 条件下， 反应 10.5h， 生成 (1S)-N-[(1S)-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]ethyl]-1-phenylethanamine
  参考文献：
  名称：

  Highly Diastereoselective Hydrogenation of Imines by a Bimetallic Pd−Cu Heterogeneous Catalyst

  摘要：

  An efficient and practical heterogeneous bimetallic Pd-Cu/C catalyst was identified as an alternative to Raney nickel for the highly diastereoselective hydrogenation of imines prepared from prochiral ketones and alpha-phenylethylamines. Chiral amines were obtained with diastereomeric excess (de) up to 94% using Pd-Cu/C, while conventional Pd-C catalysts afforded only 72% de. Optimization showed that a robust process required a palladium/copper ratio of 4:1. Evidence for the influence of catalyst pretreatment which may change the structure of the catalyst and/or metal oxidation states on the selectivity of the reaction is discussed. The bimetallic catalyst system provided consistent results on scale and performed reliably on a variety of substrates.

  DOI：

  10.1021/op1001325