4-[(三氟乙酰基)氨基]苯乙酰氯 | 113180-63-5

• 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]苯乙酰氯
• 英文名称: 4-<(trifluoroacetyl)amino>benzeneacetyl chloride
• 英文别名: 4-(trifluoroacetamido)phenylacetic acid chloride；p-Trifluoroacetamidophenylacetyl chloride；2-[4-[(2,2,2-Trifluoroacetyl)amino]phenyl]acetyl chloride
• CAS: 113180-63-5
• 化学式: C₁₀H₇ClF₃NO₂
• 分子量: 265.619
• InChiKey: LZKJNEPCXHNEDR-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  347.7±42.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(三氟乙酰基)氨基]苯乙酰氯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 2-(4-aminophenyl)-N-(1-phenylethyl)acetamide
  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
• 作为产物：
  描述：

  2-(4-(2,2,2-trifluoroacetamido)phenyl)acetic acid 在 氯化亚砜 作用下， 反应 5.0h， 以98%的产率得到4-[(三氟乙酰基)氨基]苯乙酰氯
  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

• Antibodies which catalyze hydrolysis of ester bonds
  申请人：Scripps Clinic and Research Foundation

  公开号：US05030717A1

  公开（公告）日：1991-07-09

  An analog-ligand having a conformation that substantially corresponds to the conformation of a hydrolytic transition state of an amide or ester reactant ligand is used to produce receptor molecules of predetermined specificity. The receptor molecules include an antibody combining site that binds to a reactant ligand and thereby stabilizes the tetrahedral carbon atom of the amide or ester hydrolysis transition state of that reactant ligand to catalytically hydrolyze the reactant ligand at a predetermined site.

  具有与酰胺或酯反应物配体的水解过渡态构象基本对应的模拟配体用于产生具有预定特异性的受体分子。这些受体分子包括一个与反应物配体结合的抗体结合位点，从而稳定酰胺或酯水解过渡态的四面体碳原子，以在预定位置催化水解反应物配体。
• Molecules with antibody combining sites that exhibit catalytic properties
  申请人：SCRIPPS CLINIC AND RESEARCH FOUNDATION

  公开号：EP0260939A2

  公开（公告）日：1988-03-23

  An analog-ligand having a conformation that substantially corresponds to the conformation of a hydrolytic transition state of an amide or ester reactant ligand is used to produce receptor molecules of predetermined specificity. The receptor molecules include an antibody combining site that binds to a reactant ligand and thereby stabilizes the tetrahedral carbon atom of the amide or ester hydrolysis transition state of that reactant ligand to catalytically hydrolyze the reactant ligand at a predetermined site.

  模拟配体具有与酰胺或酯类反应配体的水解过渡态构象基本一致的构象，可用于生产具有预定特异性的受体分子。 受体分子包括一个抗体结合位点，该位点与反应配体结合，从而稳定该反应配体的酰胺或酯类水解过渡态的四面体碳原子，在预定位点催化反应配体水解。
• Antibody catalysis approaching the activity of enzymes
  作者：Alfonso. Tramontano、Adrian A. Ammann、Richard A. Lerner

  DOI：10.1021/ja00215a045

  日期：1988.3
• 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：——
• US5030717A
  申请人：——

  公开号：US5030717A

  公开（公告）日：1991-07-09