4-Methoxy-N-((1S,2R)-2-methyl-3-oxo-1,3-diphenyl-propyl)-benzamide | 131371-78-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-Methoxy-N-((1S,2R)-2-methyl-3-oxo-1,3-diphenyl-propyl)-benzamide
• CAS: 131371-78-3
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: NKTZKUZTTWZJAO-VGSWGCGISA-N

反应信息

• 作为反应物：
  描述：

  4-Methoxy-N-((1S,2R)-2-methyl-3-oxo-1,3-diphenyl-propyl)-benzamide 在 二异丁基氢化铝 、 zinc(II) chloride 作用下， 生成 (1S*,2S*,3R*)-2-Methyl-3-<(p-methoxybenzoyl)amino>-1,3-diphenyl-1-propanol 、 (1R*,2S*,3R*)-2-Methyl-3-<(p-methoxybenzoyl)amino>-1,3-diphenyl-1-propanol
  参考文献：
  名称：

  Stereoselective synthesis of 1,3-amino alcohols and 1,3-amino ketones

  摘要：

  Syn,anti-N-Alkyl-1,3-amino alcohols 2 with three chiral centers are synthesized with high stereoselectively by reduction of the corresponding anti-N-acylamino ketones 1 with LiAlH4/TiCl4. The intermediate N-acylamino alcohols 3 can be isolated when DIBALH/ZnCl2 is used instead of the prior reducing system. Cyclic models are proposed to explain the steric course of the reaction in both cases. On the other hand, hydrolysis of tetrahydropyrimidines 8 with 1 N HCl at 25-degrees-C leads to syn-1,3-amino ketones 9 with high stereoselectivity. Several reducing reagents and conditions are tested in the conversion of syn-9 into the subsequent 1,3-amino alcohols. DIBALH/ZnCl2 gives the best results in the last reaction leading to syn,syn-1,3-amino alcohols 10 as practically a single diastereoisomer.

  DOI：

  10.1021/jo00030a033