(2R)-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid | 861896-81-3

• 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-{[(1R)-1-phenylethyl]amino}butanoic acid
• 英文别名: (2R)-4-oxo-4-phenyl-2-[[(1R)-1-phenylethyl]amino]butanoic acid
• CAS: 861896-81-3
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: UYSCCJDWKFPZAD-CZUORRHYSA-N

物化性质

• 熔点：
  194-196 °C(Solv: acetonitrile (75-05-8); water (7732-18-5))
• 沸点：
  491.9±45.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (2R)-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid 生成 3-苯甲酰丙烯酸
  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
• 作为产物：
  描述：

  反式-3-苯甲酰丙烯酸 、 R(+)-alpha-甲基苄胺 以 甲醇 为溶剂， 生成 (2S)-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}-butanoic acid 、 (2R)-4-oxo-4-phenyl-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

• Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues
  作者：Andrej Ďuriš、Tomáš Wiesenganger、Daniela Moravčíková、Peter Baran、Jozef Kožíšek、Adam Daïch、Dušan Berkeš

  DOI：10.1021/ol2001057

  日期：2011.4.1

  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.
• 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.
• The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction
  作者：Pavol Jakubec、Pavel Petráš、Andrej Ďuriš、Dušan Berkeš

  DOI：10.1016/j.tetasy.2009.12.014

  日期：2010.1

  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