(S)-2-hydroxy-N-(4-methoxybenzyl)-3-phenyl-propionamide | 918161-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-hydroxy-N-(4-methoxybenzyl)-3-phenyl-propionamide
• 英文别名: (S)-1-(4-methoxybenzyl)carbamoyl-2-phenylethanol；(2S)-2-hydroxy-N-[(4-methoxyphenyl)methyl]-3-phenylpropanamide
• CAS: 918161-08-7
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: RFTCBKPHURLESP-INIZCTEOSA-N

物化性质

• 熔点：
  78-80 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  531.3±50.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-N-(4-methoxybenzyl)-3-phenyl-propionamide 在 palladium on activated charcoal 、 苯并-15-冠醚-5 三乙烯二胺 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium azide 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 107.5h， 生成 D-苯丙氨酸
  参考文献：
  名称：

  Multicomponent diversity and enzymatic enantioselectivity as a route towards both enantiomers of α-amino acids—a model study

  摘要：

  A model study on a new, enantioconvergent method for the synthesis of chiral, nonracemic alpha-amino acids is presented. alpha-Acetoxyamides obtained in a Passerini multicomponent reaction are selectively hydrolyzed by Wheat Germ lipase. Studies on conversion of the thus obtained, enantiomerically enriched alpha-hydroxyamides into alpha-aminoamides are presented. Products of these reactions are then hydrolyzed to give alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.014
• 作为产物：
  描述：

  (R)-2-hydroxy-N-(4-methoxybenzyl)-3-phenyl-propionamide 在 sodium hydroxide 、 crown ether 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.33h， 生成 (S)-2-hydroxy-N-(4-methoxybenzyl)-3-phenyl-propionamide
  参考文献：
  名称：

  Multicomponent diversity and enzymatic enantioselectivity as a route towards both enantiomers of α-amino acids—a model study

  摘要：

  A model study on a new, enantioconvergent method for the synthesis of chiral, nonracemic alpha-amino acids is presented. alpha-Acetoxyamides obtained in a Passerini multicomponent reaction are selectively hydrolyzed by Wheat Germ lipase. Studies on conversion of the thus obtained, enantiomerically enriched alpha-hydroxyamides into alpha-aminoamides are presented. Products of these reactions are then hydrolyzed to give alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.014

文献信息

• Studies on the application of the Passerini reaction and enzymatic procedures to the synthesis of tripeptide mimetics
  作者：Wiktor Szymanski、Magdalena Zwolinska、Ryszard Ostaszewski

  DOI：10.1016/j.tet.2007.05.044

  日期：2007.8

  A new, efficient method for the multicomponent synthesis of tripeptide mimetics is presented. Simple, chemoenzymatic transformations of Passerini reaction products enable the introduction of varied amino acid moieties into the tripeptide scaffold, with control of the stereochemistry. Additionally, this method allows the convenient introduction of a methyl group to the amide nitrogen, leading to derivatives

  提出了一种新的，高效的三肽模拟物多组分合成方法。Passerini反应产物的简单，化学酶促转化使得能够在控制立体化学的情况下将各种氨基酸部分引入三肽支架中。另外，该方法允许将甲基方便地引入到酰胺氮中，从而生成N-甲基化氨基酸的衍生物-药物化学上令人感兴趣的化合物。
• Multicomponent diversity and enzymatic enantioselectivity as a route towards both enantiomers of α-amino acids—a model study
  作者：Wiktor Szymanski、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2006.09.014

  日期：2006.10

  A model study on a new, enantioconvergent method for the synthesis of chiral, nonracemic alpha-amino acids is presented. alpha-Acetoxyamides obtained in a Passerini multicomponent reaction are selectively hydrolyzed by Wheat Germ lipase. Studies on conversion of the thus obtained, enantiomerically enriched alpha-hydroxyamides into alpha-aminoamides are presented. Products of these reactions are then hydrolyzed to give alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.