(2R)-4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: UYSCCJDWKFPZAD-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 反式-3-苯甲酰丙烯酸 以 甲醇 为溶剂， 反应 16.0h， 生成 (2R)-4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid 、 (2S)-4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid
  参考文献：
  名称：

  A highly efficient asymmetric synthesis of methoxyhomophenylalanine using michael addition of phenethylamine

  摘要：

  A practical method for (S)-p-methoxyhomophenylalanine (S)-1 by using diastereoselective Michael addition as a key step was reported. Thus, the Michael addition of(S)1-phenethylamine (S)-3 to p-methoxy-trans-benzoylacrylic acid 2 was performed in a highly stereoselective (up to 98% d.e. and up to 90% yield) fashion and, subsequently, the resultant adduct 4a was catalytically hydrogenated to afford (S)-1 almost quantitatively. The most likely mechanism of the addition reaction was dynamic resolution. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02023-1