(2R)-4-(methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}-butanoic acid | 861896-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-4-(methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}-butanoic acid
• CAS: 861896-82-4
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: DRCJFORBEVLWTQ-RHSMWYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R)-4-(methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}-butanoic acid 在 盐酸 、 sodium tetrahydroborate 、 20 wt% Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 20.0~80.0 ℃ 、110.0 kPa 条件下， 反应 4.25h， 生成 (1R,3R)-3-amino-1-(4-methylphenyl)butane-1,4-diol acetate
  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 、 trans-3-(4-甲基苯甲酰)丙烯酸 以 甲醇 为溶剂， 生成 (2R)-4-(methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}-butanoic acid 、 (2S)-4-(methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}-butanoic acid
  参考文献：
  名称：

  Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids

  摘要：

  Acid-catalyzed lactonization in dilute hydrochloric acid of N-substituted 2-amino-4-aryl-4-hydroxybutanoic acids with electron donating aryl substituents is stereoconvergent. The stereochemical outcome is controlled by the precipitation of little soluble cis-lactones, starting from both syn-2-amino-4-aryl-4-hydroxybutanoic acids and anti-2-amino-4-aryl-4-hydroxybutanoic acids or their mixtures. A highly diastereoselective two-step sequence (acid-catalyzed lactonization with CIAT process followed by alkaline hydrolysis) for the transformation of syn-3b-d to the corresponding anti-3b-d is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.024