N-(2-oxo-2-(4-phenylbutan-2-ylamino)ethyl)benzamide | 1222802-26-7

• 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: N-(2-oxo-2-(4-phenylbutan-2-ylamino)ethyl)benzamide
• 英文别名: N-[2-oxo-2-[[(2S)-4-phenylbutan-2-yl]amino]ethyl]benzamide
• CAS: 1222802-26-7
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: JPXPFTYIZKVQGG-HNNXBMFYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  587.9±43.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苯甲酰基甘氨酸2,2,2-三氟乙酯 、 (S)-(+)-1-甲基-3-苯基丙胺 在 immobilized Protex 50FP 作用下， 以 3-甲基-3-戊醇 为溶剂， 生成 N-(2-oxo-2-(4-phenylbutan-2-ylamino)ethyl)benzamide
  参考文献：
  名称：

  Proteases screening for the kinetic resolution of amines with N-acyl α-amino acid trifluoromethyl esters: automated docking approach of binding energies using Subtilisin Novo as a prototype for serine proteases

  摘要：

  The screening of a panel of 17 proteases resulted in the selection of 4 serine proteases for the resolution of 3-amino-1-phenylbutane. The latter were used to determine the best acyl donor from a series of N-acyl alpha-amino acid trifluoroethyl esters selected as peptide mimetics (E factor up to 99). The results were correlated to an automated docking determination of their binding affinities for Subtilisin Novo. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.013

文献信息

• N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate
  作者：Malek Nechab、Lahssen El Blidi、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1039/b812089g

  日期：——

  Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h.

  通过使用碱性蛋白酶作为催化剂，N-辛酰基甘氨酸三氟乙基酯作为酰基供体，可以实现脂肪族和苄基胺类的酶动力学拆分，从而生成（S）-酰胺。对映选择性在4至244之间，而反应时间则大大缩短，在15分钟至6小时之间。