4-[(三氟乙酰基)氨基]苯乙酸乙酯 | 88975-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(三氟乙酰基)氨基]苯乙酸乙酯
• 英文名称: ethyl 4-<(trifluoroacetyl)amino>benzeneacetate
• 英文别名: Ethyl 4-(trifluoroacetamido)benzeneacetate；Ethyl 4-((trifluoroacetyl)amino)benzeneacetate；ethyl 2-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]acetate
• CAS: 88975-34-2
• 化学式: C₁₂H₁₂F₃NO₃
• 分子量: 275.227
• InChiKey: OHCBMVHZRLQPOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(三氟乙酰基)氨基]苯乙酸乙酯 在 乙醇 、 硫氰酸铵 、 sodium 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.5h， 生成
  参考文献：
  名称：

  Studies on the synthesis and analgesic and anti-inflammatory activities of 2-thiazolylamino- and 2-thiazolyloxy-arylacetic acid derivatives.

  摘要：

  根据Hantzsch方法，通过硫酰胺与卤代乙缩醛的缩合反应制备了一系列2-噻唑基氨基、2-噻唑基氧和2-噻唑基硫代芳基乙酸衍生物，而具有α-甲基芳基乙酸部分的硫酰胺则通过结合已知方法从卤代芳香硝基化合物中方便地获得。在O-苯基硫代氨基甲酸酯（XVIII）与氯代二乙缩醛的模型反应中，分离出无环卤代化合物（XIX）和4-乙氧基-2-苯氧基-2-噻唑啉（XX）等中间体，阐明了苯氧噻唑（XXI）的生成反应途径。通过小鼠的醋酸引起的扭体法和大鼠的角叉菜胶引起的足跖肿胀法，分别评估了所研究化合物的镇痛和抗炎作用。2-[4-（2-噻唑氧基）苯基]丙酸（XIVa）在活性与毒性之间具有最佳的治疗比（在小鼠中）。

  DOI：

  10.1248/cpb.31.3424
• 作为产物：
  描述：

  2-(4-(2,2,2-trifluoroacetamido)phenyl)acetic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-[(三氟乙酰基)氨基]苯乙酸乙酯
  参考文献：
  名称：

  Catalytic antibodies with acyl-transfer capabilities: mechanistic and kinetic investigations

  摘要：

  Antibodies have been shown to catalyze acyl-transfer reactions. The processes by which they perform such tasks have often been postulated but largely remain unknown. An extended study is presented on three different monoclonal antibodies that catalyze the hydrolysis of an alkyl ester and an aryl amide bond. Antibodies 2H6 and 21H3 catalyze the hydrolysis of an unactivated benzyl ester and show exquisite specificity for substrates with either the R or S configuration, respectively, while 43C9 catalyzes the cleavage of a p-nitroanilide amide bond. New substrates were synthesized and buffer-assisted reactions were employed to determine antibody-substrate fidelity. Oxygen-18 incorporation experiments were performed providing evidence that these antibody-mediated reactions proceed through attack at the acyl carbonyl, and excluding the possibility of an S(N)2 displacement; mechanism for the ester hydrolysis reaction. A ph-rate profile study in protium and deuterium oxide was performed on antibody 43C9. This revealed an apparent PK(a) of approximately 9 involved in catalysis, but both the presence and absence of a solvent isotope effect in the ph-dependent and -independent regions suggested a multistep reaction pathway may be operative.

  DOI：

  10.1021/ja00001a042

文献信息

• JANDA, KIM D.;ASHLEY, JON A.;JONES, TERESA M.;MCLEOD, DONALD A.;SCHLOEDER+, J. AMER. CHEM. SOC., 113,(1991) N, C. 291-297
  作者：JANDA, KIM D.、ASHLEY, JON A.、JONES, TERESA M.、MCLEOD, DONALD A.、SCHLOEDER+

  DOI：——

  日期：——
• US5712389A
  申请人：——

  公开号：US5712389A

  公开（公告）日：1998-01-27
• US5919432A
  申请人：——

  公开号：US5919432A

  公开（公告）日：1999-07-06
• Studies on the synthesis and analgesic and anti-inflammatory activities of 2-thiazolylamino- and 2-thiazolyloxy-arylacetic acid derivatives.
  作者：RYOZO MAEDA、EIICHI OHSUGI、TOSHIHIRO FUJIOKA、KATSUMI HIROSE

  DOI：10.1248/cpb.31.3424

  日期：——

  A series of 2-thiazolylamino-, 2-thiazolyloxy- and 2-thiazolylthio-arylacetic acid derivatives was prepared by condensation of thioamides with halo-acetals according to Hantzsch's method, and thioamides having the α-methylarylacetic acid moiety were conveniently obtained from haloaromatic nitro compounds by a combination of known methods. In the model reaction of O-phenyl thiocarbamate (XVIII) with chloro-diethylacetal, isolation of intermediates such as acyclic halo-compound (XIX) and 4-ethoxy-2-phenoxy-2-thiazoline (XX) clarified the reaction path for the formation of 2-phenoxythiazole (XXI). The analgesic and anti-inflammatory effects of the compounds studied were evaluated by using the acetic acid-induced writhing method in mice and the rat carrageenin paw edema method, respectively. 2- [4- (2-Thiazolyloxy) phenyl] propionic acid (XIVa) had the most favorable therapeutic ratio between activity and toxicity (in mice).

  根据Hantzsch方法，通过硫酰胺与卤代乙缩醛的缩合反应制备了一系列2-噻唑基氨基、2-噻唑基氧和2-噻唑基硫代芳基乙酸衍生物，而具有α-甲基芳基乙酸部分的硫酰胺则通过结合已知方法从卤代芳香硝基化合物中方便地获得。在O-苯基硫代氨基甲酸酯（XVIII）与氯代二乙缩醛的模型反应中，分离出无环卤代化合物（XIX）和4-乙氧基-2-苯氧基-2-噻唑啉（XX）等中间体，阐明了苯氧噻唑（XXI）的生成反应途径。通过小鼠的醋酸引起的扭体法和大鼠的角叉菜胶引起的足跖肿胀法，分别评估了所研究化合物的镇痛和抗炎作用。2-[4-（2-噻唑氧基）苯基]丙酸（XIVa）在活性与毒性之间具有最佳的治疗比（在小鼠中）。
• Catalytic antibodies with acyl-transfer capabilities: mechanistic and kinetic investigations
  作者：Kim D. Janda、Jon A. Ashley、Teresa M. Jones、Donald A. McLeod、Diane M. Schloeder、Michael I. Weinhouse、Richard A. Lerner、Richard A. Gibbs、Patricia A. Benkovic

  DOI：10.1021/ja00001a042

  日期：1991.1

  Antibodies have been shown to catalyze acyl-transfer reactions. The processes by which they perform such tasks have often been postulated but largely remain unknown. An extended study is presented on three different monoclonal antibodies that catalyze the hydrolysis of an alkyl ester and an aryl amide bond. Antibodies 2H6 and 21H3 catalyze the hydrolysis of an unactivated benzyl ester and show exquisite specificity for substrates with either the R or S configuration, respectively, while 43C9 catalyzes the cleavage of a p-nitroanilide amide bond. New substrates were synthesized and buffer-assisted reactions were employed to determine antibody-substrate fidelity. Oxygen-18 incorporation experiments were performed providing evidence that these antibody-mediated reactions proceed through attack at the acyl carbonyl, and excluding the possibility of an S(N)2 displacement; mechanism for the ester hydrolysis reaction. A ph-rate profile study in protium and deuterium oxide was performed on antibody 43C9. This revealed an apparent PK(a) of approximately 9 involved in catalysis, but both the presence and absence of a solvent isotope effect in the ph-dependent and -independent regions suggested a multistep reaction pathway may be operative.