(S)-2-benzoylamino-4-phenylbutyric acid | 150446-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-benzoylamino-4-phenylbutyric acid
• 英文别名: N-benzoyl-L-homophenylalanine；(S)-2-benzamido-4-phenylbutanoic acid；N-benzoyl homophenylalanine；(2S)-2-benzamido-4-phenylbutanoic acid
• CAS: 150446-13-2
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: KYQLWMGRTKMDAA-HNNXBMFYSA-N

物化性质

• 沸点：
  539.1±43.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-benzoylamino-4-phenylbutyric acid 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到4-phenethyl-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  Peptide-Catalyzed Conversion of Racemic Oxazol-5(4H)-ones into Enantiomerically Enriched α-Amino Acid Derivatives

  摘要：

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

  DOI：

  10.1021/jo402828f
• 作为产物：
  描述：

  (2S)-2-(甲氧基甲基)-N-(3-苯基亚丙基)-1-吡咯烷胺 在 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 sodium periodate 、 正丁基锂 、 samarium diiodide 、 ruthenium(III) trichloride hydrate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 (S)-2-benzoylamino-4-phenylbutyric acid
  参考文献：
  名称：

  Asymmetric synthesis of ?-(heteroaryl)alkylamines and ?-amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones

  摘要：

  第 V 组金属化合物与三氧化硫的反应

  DOI：

  10.3906/kim-1302-71

文献信息

• Hexahydronaphth[1,2-b]-1,4-oxazines
  申请人：Merck & Co., Inc.

  公开号：US04420480A1

  公开（公告）日：1983-12-13

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display .alpha..sub.2 -adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamidotetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘并[1,2-b]-1,4-噁唑具有多巴胺能活性，并表现出.alpha..sub.2-肾上腺素受体拮抗作用。它们在帕金森病、抑郁症和高血压的治疗中很有用。一种重要的制备方法是通过环合成适当的2-氯乙酰胺四氢萘酚-1-醇，并还原所得的环状酰胺羰基团。
• Hexahydronaphth(1,2-b)-1,4-oxazines, process for their preparation and pharmaceutical formulation containing them
  申请人：Merck & Co., Inc.

  公开号：EP0080115A2

  公开（公告）日：1983-06-01

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display α2-adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamido- tetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘并[1,2-b]-1,4-噁嗪具有多巴胺能活性，并显示出α2-肾上腺素能受体拮抗作用。 它们可用于治疗帕金森病、抑郁症和高血压。 一种重要的制备方法是将适当的 2-氯乙酰胺基四氢萘-1-醇闭环，并还原由此产生的环状酰胺羰基。
• Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
  作者：Raquel Almansa、Juan F. Collados、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2010.03.046

  日期：2010.6

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of nonproteinogenic amino acids with l-amino acid transaminase: synthesis of (2S)-2-amino-4-oxo-4-phenylbutyric and (3E,2S)-2-amino-4-phenylbutenoic acids
  作者：Nitin W. Fadnavis、Su-Hyun Seo、Joo-Hyun Seo、Byung-Gee Kim

  DOI：10.1016/j.tetasy.2006.07.034

  日期：2006.9

  2,4-Dioxo-4-phenylbutyric acid and 2-oxo-4-phenylbut-3-enoic acid are converted to the corresponding (S)-2-amino acids by recombinant Escherichia coli whole cells over-expressing aromatic transaminase from Enterobacter sp. BK2K-1 (AroATEs) in high yields (68-78%) and high enantiomeric purity (> 99%) using L-aspartic acid as an amino donor. (c) 2006 Elsevier Ltd. All rights reserved.
• US4420480A
  申请人：——

  公开号：US4420480A

  公开（公告）日：1983-12-13