rac-4,4-difluoro-3-(N-phenylacetylamino)butanoic acid | 160617-36-7

• 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: rac-4,4-difluoro-3-(N-phenylacetylamino)butanoic acid
• 英文别名: 4,4-Difluoro-3-[(2-phenylacetyl)amino]butanoic acid
• CAS: 160617-36-7
• 化学式: C₁₂H₁₃F₂NO₃
• 分子量: 257.237
• InChiKey: LAGHQOUJNYYUKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-4,4-difluoro-3-(N-phenylacetylamino)butanoic acid 生成 (S)-4,4-difluoro-3-(N-phenylacetylamino)butanoic acid
  参考文献：
  名称：

  Biocatalytic resolution of β-fluoroalkyl-β-amino acids

  摘要：

  N-Phenylacetyl derivatives of beta-fluoroalkyl-beta-alanines 6 were synthesized and biocatalytically resolved to the corresponding enantiopure beta-amino acids 7, 9 with the aid of penicillin acylase (EC 3.5.1.11) from Escherichia coli. In substrates 6 the enantioselectivity of the biocatalytic process was practically uninfluenced by the nature of the fluoroalkyl chain. Thus, beta-fluoroalkyl-beta-alanines 7, 9 bearing short (R = CF3, CHF2) or long [C3F7, H(CF2)(4)] chains were prepared in high enantiomeric purity. The (R)-enantiomer was the fast-reacting enantiomer in all cases.

  DOI：

  10.1016/0957-4166(94)80063-4
• 作为产物：
  描述：

  4,4-difluoro-3-aminobutanoic acid 、 苯乙酰氯 在 potassium hydrogencarbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以98%的产率得到rac-4,4-difluoro-3-(N-phenylacetylamino)butanoic acid
  参考文献：
  名称：

  Biocatalytic resolution of β-fluoroalkyl-β-amino acids

  摘要：

  N-Phenylacetyl derivatives of beta-fluoroalkyl-beta-alanines 6 were synthesized and biocatalytically resolved to the corresponding enantiopure beta-amino acids 7, 9 with the aid of penicillin acylase (EC 3.5.1.11) from Escherichia coli. In substrates 6 the enantioselectivity of the biocatalytic process was practically uninfluenced by the nature of the fluoroalkyl chain. Thus, beta-fluoroalkyl-beta-alanines 7, 9 bearing short (R = CF3, CHF2) or long [C3F7, H(CF2)(4)] chains were prepared in high enantiomeric purity. The (R)-enantiomer was the fast-reacting enantiomer in all cases.

  DOI：

  10.1016/0957-4166(94)80063-4

文献信息

• Biocatalytic resolution of β-fluoroalkyl-β-amino acids
  作者：Vadim A. Soloshonok、Alexander G. Kirilenko、Nataly A. Fokina、Irine P. Shishkina、Sergey V. Galushko、Valery P. Kukhar、Vytas K. Švedas、Elena V. Kozlova

  DOI：10.1016/0957-4166(94)80063-4

  日期：1994.6

  N-Phenylacetyl derivatives of beta-fluoroalkyl-beta-alanines 6 were synthesized and biocatalytically resolved to the corresponding enantiopure beta-amino acids 7, 9 with the aid of penicillin acylase (EC 3.5.1.11) from Escherichia coli. In substrates 6 the enantioselectivity of the biocatalytic process was practically uninfluenced by the nature of the fluoroalkyl chain. Thus, beta-fluoroalkyl-beta-alanines 7, 9 bearing short (R = CF3, CHF2) or long [C3F7, H(CF2)(4)] chains were prepared in high enantiomeric purity. The (R)-enantiomer was the fast-reacting enantiomer in all cases.