(2R)-4-(3,4-dimethoxyphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid | 1220353-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-4-(3,4-dimethoxyphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid
• 英文别名: (2R)-4-(3,4-dimethoxyphenyl)-4-oxo-2-[[(1R)-1-phenylethyl]amino]butanoic acid
• CAS: 1220353-57-0
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: SUKZCNMTULJLCF-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-4-(3,4-dimethoxyphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues

  摘要：

  The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.

  DOI：

  10.1021/ol2001057
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 乙醛酸 、 3,4-二甲氧基苯乙酮 以 乙醇 为溶剂， 反应 144.0h， 以51%的产率得到(2R)-4-(3,4-dimethoxyphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid
  参考文献：
  名称：

  The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction

  摘要：

  The novel synthesis of highly enantioenriched N-substituted alpha-amino-gamma-alkyl(aryl)-gamma-oxoutanoic acids is described The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed. (c) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.014