3-氨基-4,4,4-三氟丁酸甲酯 | 748746-28-3

• 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
• 中文名称: 3-氨基-4,4,4-三氟丁酸甲酯
• 英文名称: Methyl 3-amino-4,4,4-trifluorobutyrate
• 英文别名: methyl 3-amino-4,4,4-trifluorobutanoate
• CAS: 748746-28-3
• 化学式: C₅H₈F₃NO₂
• 分子量: 171.119
• InChiKey: YOBIFUUUJYCCFN-UHFFFAOYSA-N

物化性质

• 沸点：
  50 °C/1 mmHg
• 密度：
  1.293 g/mL at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37
• 危险类别码：
  R36/37/38,R43
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基-4,4,4-三氟丁酸甲酯 在 盐酸 、 氨 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis, and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-Diaminopropionic acid derivatives as surrogates of aspartic acid

  摘要：

  In an effort to discover novel nonpeptide glycoprotein IIb/IIIa (GPIIb/lIIa, alpha(IIb)/beta 3) inhibitors, we investigated RGD mimetics featuring a 3-substituted benzoic acid as the core, benzamidine as the basic moiety, and a series of beta- and alpha-substituted beta-alanine derivatives as aspartic acid surrogates. It was found that the use of beta-methyl beta-alanine slightly improved the anti-aggregant potency in human platelet-rich plasma over the unsubstituted beta-alanine compound, while alpha-substitution with a trifluoromethyl group resulted in considerable loss in activity. Significant enhancement (up to 100-fold) in potency was obtained when the beta-alanine was replaced with N-2-substituted L-2,3-diaminopropionic acid derivatives. Among the three types of cc-substituents (carbamate, amide, and sulfonamide) investigated, no apparent preference was observed with respect to in vitro potency. However, alkyl groups were more favorable than arylalkyl groups (Cbz) in the carbamate analogues. We also investigated piperidine, piperazine, and N-formamidinopiperidine as replacements for the benzamidine moiety. The former two replacements led to a drop in potency while the latter replacement resulted in maintenance of activity as compared with the corresponding benzamidine analogue. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00013-8
• 作为产物：
  描述：

  methyl 3-(benzylideneamino)-4,4,4-trifluorobutyrate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 3-氨基-4,4,4-三氟丁酸甲酯
  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

• Design, synthesis, and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-Diaminopropionic acid derivatives as surrogates of aspartic acid
  作者：Chu-Biao Xue、John Roderick、Sharon Jackson、Maria Rafalski、Arlene Rockwell、Shaker Mousa、Richard E. Olson、William F. DeGrado

  DOI：10.1016/s0968-0896(97)00013-8

  日期：1997.4

  In an effort to discover novel nonpeptide glycoprotein IIb/IIIa (GPIIb/lIIa, alpha(IIb)/beta 3) inhibitors, we investigated RGD mimetics featuring a 3-substituted benzoic acid as the core, benzamidine as the basic moiety, and a series of beta- and alpha-substituted beta-alanine derivatives as aspartic acid surrogates. It was found that the use of beta-methyl beta-alanine slightly improved the anti-aggregant potency in human platelet-rich plasma over the unsubstituted beta-alanine compound, while alpha-substitution with a trifluoromethyl group resulted in considerable loss in activity. Significant enhancement (up to 100-fold) in potency was obtained when the beta-alanine was replaced with N-2-substituted L-2,3-diaminopropionic acid derivatives. Among the three types of cc-substituents (carbamate, amide, and sulfonamide) investigated, no apparent preference was observed with respect to in vitro potency. However, alkyl groups were more favorable than arylalkyl groups (Cbz) in the carbamate analogues. We also investigated piperidine, piperazine, and N-formamidinopiperidine as replacements for the benzamidine moiety. The former two replacements led to a drop in potency while the latter replacement resulted in maintenance of activity as compared with the corresponding benzamidine analogue. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.
• 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.