ethyl 4-<(4-carboxy-1-oxobutyl)amino>benzeneacetate | 130468-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-<(4-carboxy-1-oxobutyl)amino>benzeneacetate
• 英文别名: 5-[4-(2-ethoxy-2-oxoethyl)anilino]-5-oxopentanoic acid
• CAS: 130468-89-2
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: YRSOOTNGFZGJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-<(4-carboxy-1-oxobutyl)amino>benzeneacetate 、 水 生成 乙醇
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  4-[(三氟乙酰基)氨基]苯乙酰氯 在 吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 ethyl 4-<(4-carboxy-1-oxobutyl)amino>benzeneacetate
  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