4,4-difluoro-3-aminobutanoic acid | 77162-46-0

• 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: 4,4-difluoro-3-aminobutanoic acid
• 英文别名: 3-Amino-4,4-difluorobutanoic acid
• CAS: 77162-46-0
• 化学式: C₄H₇F₂NO₂
• mdl: MFCD24392278
• 分子量: 139.102
• InChiKey: OLFYIMZVBDNOOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4,4-Difluoro-3-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid ethyl ester 在 盐酸 作用下， 反应 6.0h， 生成 4,4-difluoro-3-aminobutanoic acid
  参考文献：
  名称：

  Transamination of fluorinated β-keto carboxylic esters. A biomimetic approach to β-polyfluoroalkyl-β-amino acids.

  摘要：

  The base-catalyzed isomerization of N-benzylimines (or enamines) of beta-polyfluoroalkyl-beta-ketocarboxylic esters cleanly affords the N-benzylidene derivatives of beta-polyfluoro-beta-aminocarboxylic esters which are hydrolyzed to corresponding amino acids in high overall yields.

  DOI：

  10.1016/s0040-4039(00)73652-5

文献信息

• Biomimetic base-catalyzed [1,3]-proton shift reaction. A practical synthesis of β-fluoroalkyl-β-amino acids
  作者：Vadim A. Soloshonok、Valery P. Kukhar

  DOI：10.1016/0040-4020(96)00300-6

  日期：1996.5

  An efficient approach to practical synthesis of β-fluoroalkyl-β-amino acids is described. The method consists in the reducing reagent-free base-catalyzed biomimetic transamination reaction between fluorinated β-keto carboxylic esters and benzylamine. This transformation involves two sequential base-catalyzed [1,3]-proton transfers giving rise to corresponding N-benzylidene derivatives as the products

  描述了一种有效合成β-氟烷基-β-氨基酸的有效方法。该方法在于氟化β-酮羧酸酯和苄胺之间的无还原剂的无碱催化的仿生转氨反应。该转变涉及两个连续的碱催化的[1,3]-质子转移，产生相应的N-亚苄基衍生物，作为最终热力学平衡的产物，由氟代烷基的吸电子特性指导。证明了通过应用单手性碱作为这些异构化的催化剂来催化对映体控制的靶向β-氨基酸合成的机会。
• Fluorinated methyl beta-alanine derivatives
  申请人：Merrell Toraude et Compagnie

  公开号：US04375477A1

  公开（公告）日：1983-03-01

  Beta-monofluoromethyl beta-alanine, beta-difluoromethyl beta-alanine and pharmaceutically acceptable esters and amides derived from the acid group, amides derived from the amine group, and salts thereof are novel compounds which inhibit .gamma.-aminobutyric acid transaminase (GABA-T).

  Beta-monofluoromethyl beta-alanine，beta-difluoromethyl beta-alanine以及从酸基衍生的药用可接受的酯和酰胺，从胺基衍生的酰胺和它们的盐是新的化合物，可以抑制γ-氨基丁酸转氨酶（GABA-T）。
• Transamination of fluorinated β-keto carboxylic esters. A biomimetic approach to β-polyfluoroalkyl-β-amino acids.
  作者：Vadim A. Soloshonok、Alexander G. Kirilenko、Valery P. Kukhar'、Giuseppe Resnati

  DOI：10.1016/s0040-4039(00)73652-5

  日期：1993.5

  The base-catalyzed isomerization of N-benzylimines (or enamines) of beta-polyfluoroalkyl-beta-ketocarboxylic esters cleanly affords the N-benzylidene derivatives of beta-polyfluoro-beta-aminocarboxylic esters which are hydrolyzed to corresponding amino acids in high overall yields.
• 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.