(2R,4S)-4-hydroxy-4-(4-methoxyphenyl)-2-{[(1R)-1-phenylethyl]amino}butanoic acid | 861896-86-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4S)-4-hydroxy-4-(4-methoxyphenyl)-2-{[(1R)-1-phenylethyl]amino}butanoic acid
• 英文别名: (2R,4S)-4-hydroxy-4-(4-methoxyphenyl)-2-[[(1R)-1-phenylethyl]amino]butanoic acid
• CAS: 861896-86-8
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: WEKMXMNFLDQLDV-XWIAVFTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-hydroxy-4-(4-methoxyphenyl)-2-{[(1R)-1-phenylethyl]amino}butanoic acid 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 (2R,4R)-4-hydroxy-4-(4-methoxyphenyl)-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
• 作为产物：
  描述：

  (E)-4-(4-methoxyphenyl)-4-oxo-2-butenoic acid 在 sodium tetrahydroborate 、 manganese(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (2R,4S)-4-hydroxy-4-(4-methoxyphenyl)-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

文献信息

• Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids
  作者：Dušan Berkeš、Andrej Kolarovič、Robert Manduch、Peter Baran、František Považanec

  DOI：10.1016/j.tetasy.2005.04.024

  日期：2005.6

  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.