[乙酰基-(4-乙氧基苯基)氨基]2,2-二甲基丙酸酯 | 102725-57-5

• 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: [乙酰基-(4-乙氧基苯基)氨基]2,2-二甲基丙酸酯
• 中文别名: N-(特戊酰茚二酮氧基)非那西汀
• 英文名称: N-(pivaloyloxy)phenacetin
• 英文别名: (N-acetyl-4-ethoxyanilino) 2,2-dimethylpropanoate
• CAS: 102725-57-5
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: MPNGGGGXPLRSTK-UHFFFAOYSA-N

物化性质

• 沸点：
  376.7±44.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [乙酰基-(4-乙氧基苯基)氨基]2,2-二甲基丙酸酯 在 palladium on activated charcoal sodium azide 、 三(2-氯乙基)胺 、 氢气 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、344.73 kPa 条件下， 反应 16.5h， 生成 N-(3-氨基-4-乙氧基苯基)乙酰胺
  参考文献：
  名称：

  Involvement of Free Nitrenium Ions, Ion Pairs, and Preassociation Trapping in the Reactions of Ester Derivatives of N-Arylhydroxylamines and N-Arylhydroxamic Acids in Aqueous Solution

  摘要：

  Rate and product yield data for the decomposition of the ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids 1a-i in aqueous solution in the presence of N-3(-) support a mechanistic scheme (Scheme 5) in which the trapping by N-3(-) changes from trapping of the free ion, to trapping of an ion pair, to a preassociation process as the ion becomes more reactive. When the rate constant for trapping of the free ion by solvent, k(s), < similar to 10(8) s(-1), trapping by both N-3(-) and solvent occurs almost exclusively at the free ion. When 10(8) s(-1) < similar to k(s) < similar to 10(10) s(-1), a change in the mechanism occurs, and trapping of the ion pair by both solvent and N-3(-) becomes important. In this range of reactivity there is also evidence, based on the apparent magnitude of k(az)', the rate constant for N-3(-) trapping of the ion pair, that some of the reaction with N-3(-) occurs though a preassociation process. When k(s) > similar to 10(10) s(-1) essentially all of the observed N-3(-) trapping occurs by a preassociation process because N-3(-), which cannot react with the ion pair faster than the diffusion limit, can no longer compete with solvent for the ion pair. This progression in trapping mechanisms as the ion becomes more reactive with solvent is apparently an important factor in determining the carcinogenic potential of aromatic amines and amides which are metabolized into sulfuric and carboxylic acid esters of N-arylhydroxylamines and N-arylhydroxamic acids. Nitrenium ions that undergo slow reactions with solvent are selectively trapped by biologically relevant nucleophiles such as 2'-deoxyguanosine, As the rate constant for reaction with solvent increases, the nitrenium ion is no longer capable of undergoing selective trapping by nonsolvent nucleophiles because these reactions are rate limited by diffusion, but solvent trapping is not.

  DOI：

  10.1021/jo00130a034

文献信息

• Detection of N-acetyl-p-benzoquinone imine produced during the hydrolysis of the model phenacetin metabolite N-(pivaloyloxy)phenacetin
  作者：Michael Novak、Maria Pelecanou、Joseph N. Zemis

  DOI：10.1021/jm00158a018

  日期：1986.8

  N-Acetyl-p-benzoquinone imine (4) can be detected by UV spectrophotometry and HPLC during the hydrolysis of N-(pivaloyloxy)phenacetin (3c). This material serves as a model for the sulfate and glucuronide conjugates (3a and 3b) of N-hydroxyphenacetin (2). Direct detection of 4 during the hydrolysis of 3a and 3b is precluded by the extreme instability of 3a and the very slow hydrolysis of 3b. Our data

  在N-（新戊酰氧基）非那西丁（3c）水解过程中，可以通过UV分光光度法和HPLC检测N-乙酰基-对苯醌亚胺（4）。该材料可作为N-羟基非那西丁（2）的硫酸盐和葡萄糖醛酸结合物（3a和3b）的模型。3a极度不稳定和3b极慢的水解作用阻止了3a和3b水解过程中直接检测4。我们的数据表明，在1.0-8.0范围内的所有pH值下，超过90％的3c水解通过中间体4进行。我们所有的结果表明4是通过氮离子机理产生的。3b和3c水解反应中的许多差异可以用涉及紧密的和溶剂分离的氮离子对的机理来解释。其他差异可能是由于均质途径造成的，
• Involvement of Free Nitrenium Ions, Ion Pairs, and Preassociation Trapping in the Reactions of Ester Derivatives of N-Arylhydroxylamines and N-Arylhydroxamic Acids in Aqueous Solution
  作者：Michael Novak、Mary Jo Kahley、Jing Lin、Sonya A. Kennedy、Tishia G. James

  DOI：10.1021/jo00130a034

  日期：1995.12

  Rate and product yield data for the decomposition of the ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids 1a-i in aqueous solution in the presence of N-3(-) support a mechanistic scheme (Scheme 5) in which the trapping by N-3(-) changes from trapping of the free ion, to trapping of an ion pair, to a preassociation process as the ion becomes more reactive. When the rate constant for trapping of the free ion by solvent, k(s), < similar to 10(8) s(-1), trapping by both N-3(-) and solvent occurs almost exclusively at the free ion. When 10(8) s(-1) < similar to k(s) < similar to 10(10) s(-1), a change in the mechanism occurs, and trapping of the ion pair by both solvent and N-3(-) becomes important. In this range of reactivity there is also evidence, based on the apparent magnitude of k(az)', the rate constant for N-3(-) trapping of the ion pair, that some of the reaction with N-3(-) occurs though a preassociation process. When k(s) > similar to 10(10) s(-1) essentially all of the observed N-3(-) trapping occurs by a preassociation process because N-3(-), which cannot react with the ion pair faster than the diffusion limit, can no longer compete with solvent for the ion pair. This progression in trapping mechanisms as the ion becomes more reactive with solvent is apparently an important factor in determining the carcinogenic potential of aromatic amines and amides which are metabolized into sulfuric and carboxylic acid esters of N-arylhydroxylamines and N-arylhydroxamic acids. Nitrenium ions that undergo slow reactions with solvent are selectively trapped by biologically relevant nucleophiles such as 2'-deoxyguanosine, As the rate constant for reaction with solvent increases, the nitrenium ion is no longer capable of undergoing selective trapping by nonsolvent nucleophiles because these reactions are rate limited by diffusion, but solvent trapping is not.