N-phenylacetyl phenylalanine methyl ester | 138867-51-3

• 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: N-phenylacetyl phenylalanine methyl ester
• 英文别名: N-phenylacetyl-D-Phe methyl ester；N-phenylacetyl-D-phenylalanine methyl ester；(R)-methyl 3-phenyl-2-(2-phenylacetamido)propanoate；methyl (2R)-3-phenyl-2-[(2-phenylacetyl)amino]propanoate
• CAS: 138867-51-3
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: OCGCFGFKKQLWOK-MRXNPFEDSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  495.5±40.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenylacetyl phenylalanine methyl ester 在 sodium phosphate buffer 、 penicillin-G amidase from E_. coli 作用下， 反应 48.0h， 生成 D-苯丙氨酸甲酯
  参考文献：
  名称：

  Quantitative enzymatic protection of d-amino acid methyl esters by exploiting ‘relaxed’ enantioselectivity of penicillin-G amidase in organic solvent

  摘要：

  The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.153
• 作为产物：
  描述：

  D-苯丙氨酸甲酯 、 苯乙酸甲酯 在 penicillin-G amidase from E_. coli 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-phenylacetyl phenylalanine methyl ester
  参考文献：
  名称：

  Quantitative enzymatic protection of d-amino acid methyl esters by exploiting ‘relaxed’ enantioselectivity of penicillin-G amidase in organic solvent

  摘要：

  The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.153

文献信息

• Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis
  作者：Shouxin Liu、Yihua Yang、Xinwei Liu、Farhana K. Ferdousi、Andrei S. Batsanov、Andrew Whiting

  DOI：10.1002/ejoc.201300560

  日期：2013.9

  The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65–68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings

  已经研究了由芳基硼酸催化的氨基酸衍生物的直接酰胺化。相对于简单的胺-羧酸组合，该反应通常较慢，但通常在 65-68°C 下进行，避免了外消旋化。发现 3,4,5-三氟苯基硼酸和邻硝基苯基硼酸是最好的催化剂，但对于较慢的二肽形成，需要高催化剂负载量，并且发现了两种芳基硼酸之间有趣的协同催化作用。
• Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides
  作者：Pavel Starkov、Tom D. Sheppard

  DOI：10.1039/c0ob01069c

  日期：——

  with a variety of carboxylic acids and amines. With trimethyl or tris(2,2,2-trifluoroethyl) borate, amides are obtained in good to excellent yield and high purity after a simple work-up procedure. Tris(2,2,2-trifluoroethyl) borate can also be used for the straightforward conversion of primary amides to secondary amidesvia transamidation.

  简单的硼酸盐可作为与各种羧酸和胺形成酰胺键的有效促进剂。与三甲基或三（2,2,2-三氟乙基）硼酸酯通过简单的后处理程序即可获得高至优异收率和高纯度的酰胺。 三（2,2,2-三氟乙基）硼酸酯也可用于通过酰胺交换将伯酰胺直接转化为仲酰胺。
• A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids
  作者：Solmaz Fatemi、Nicolas Gernigon、Dennis G. Hall

  DOI：10.1039/c5gc00659g

  日期：——

  The development of direct and atom-economical amidation methods is of high priority because of the importance of amides and peptides as components of pharmaceuticals and commodity chemicals. This article describes...

  由于酰胺和肽作为药物和日用化学品的组成部分的重要性，直接和原子经济的酰胺化方法的开发是高度优先的。本文介绍...
• Triflic anhydride-mediated synthesis of oxazoles
  作者：Armin Thalhammer、Jasmin Mecinović、Christopher J. Schofield

  DOI：10.1016/j.tetlet.2008.12.080

  日期：2009.3

  N-Acyl amino acid esters undergo triflic anhydride-mediated cyclodehydration to form oxazoles and bisoxazoles in a simple one-pot transformation.

  N-酰基氨基酸酯经过三氟甲磺酸酐介导的环脱水，以简单的一锅法转化形成恶唑和双恶唑。
• Reduction of Sterically Hindered α,α-disubstituted Amino Esters
  作者：Peter W. Glunz、Daniel H. Rich

  DOI：10.1080/00397919908086041

  日期：1999.3

  Abstract Reductions of a series of highly hindered α,α-disubstituted amino esters to the corresponding amino alcohols were accomplished using the BuLi-DIBAl “ate complex”. In addition, the novel amino acid a-benzyl histidine was reduced via α persilylation/LAH reduction protocol.

  摘要 使用 BuLi-DIBA1 “ate 络合物”将一系列高度受阻的 α,α-二取代氨基酯还原为相应的氨基醇。此外，通过α persilyllation/LAH 还原方案还原了新型氨基酸α-苄基组氨酸。