N-acetyl-L-phenylalanine cyclohexylmethyl ester

• 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-acetyl-L-phenylalanine cyclohexylmethyl ester
• 英文别名: cyclohexylmethyl (2S)-2-acetamido-3-phenylpropanoate
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: JQWJTTQUQGKKDQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 在 palladium diacetate 、 氢氧化钾 、 KCl-Subtilisin Bacillus lentus 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 生成 N-acetyl-L-phenylalanine cyclohexylmethyl ester
  参考文献：
  名称：

  Probing the specificity of the S 1 ′, leaving group, site of subtilisin Bacillus lentus using an enzyme-catalyzed transesterification reaction

  摘要：

  Subtilisin Bacillus lentus catalyzes transesterifications between N-acetyl-L-phenylalanine vinyl ester and a wide range of alcohols. Reaction yields are high when primary alcohols are used, and quantitative with methanol. With chiral alcohols, the reaction is enantioselective, and the stereoselectivity is reversed on going from open chain secondary alcohols to beta-branched primary alcohols. A model is proposed to account for this change in absolute configuration preference. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00022-6

文献信息

• Probing the specificity of the S 1 ′, leaving group, site of subtilisin Bacillus lentus using an enzyme-catalyzed transesterification reaction
  作者：Richard C. Lloyd、Michael Dickman、J.Bryan Jones

  DOI：10.1016/s0957-4166(98)00022-6

  日期：1998.2

  Subtilisin Bacillus lentus catalyzes transesterifications between N-acetyl-L-phenylalanine vinyl ester and a wide range of alcohols. Reaction yields are high when primary alcohols are used, and quantitative with methanol. With chiral alcohols, the reaction is enantioselective, and the stereoselectivity is reversed on going from open chain secondary alcohols to beta-branched primary alcohols. A model is proposed to account for this change in absolute configuration preference. (C) 1998 Elsevier Science Ltd. All rights reserved.