N-(4-chlorophenyl)-O-pivaloylhydroxylamine | 116278-63-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-chlorophenyl)-O-pivaloylhydroxylamine
• 英文别名: (4-Chloroanilino) 2,2-dimethylpropanoate
• CAS: 116278-63-8
• 化学式: C₁₁H₁₄ClNO₂
• 分子量: 227.691
• InChiKey: BOGZWHUVVCSPKK-UHFFFAOYSA-N

物化性质

• 沸点：
  288.0±42.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-O-pivaloylhydroxylamine 在 iron(II) chloride 作用下， 以 水 、 乙腈 为溶剂， 以70.7%的产率得到对氯苯胺
  参考文献：
  名称：

  Hydrolysis and iron(2+)-induced reduction of N-aryl-O-pivaloylhydroxylamines: aqueous solution chemistry of model carcinogens

  摘要：

  DOI：

  10.1021/jo00255a018
• 作为产物：
  描述：

  特戊酰氰 、 4-氯苯基羟胺 在 N-乙基吗啉 作用下， 以 苯 为溶剂， 反应 0.33h， 以75%的产率得到N-(4-chlorophenyl)-O-pivaloylhydroxylamine
  参考文献：
  名称：

  Hydrolysis and iron(2+)-induced reduction of N-aryl-O-pivaloylhydroxylamines: aqueous solution chemistry of model carcinogens

  摘要：

  DOI：

  10.1021/jo00255a018

文献信息

• The mechanism of the interaction of N-aryl-O-pivaloylhydroxylamines with reducing metal ions
  作者：Robert K. Lagerman、Michael Novak

  DOI：10.1016/s0040-4039(00)99615-1

  日期：1989.1
• Competitive base-induced .alpha.-elimination and methanolysis of N-aryl-O-pivaloylhydroxylamines
  作者：Michael Novak、Kristy A. Martin、Julie L. Heinrich、Kristine M. Peet、Linda K. Mohler

  DOI：10.1021/jo00297a015

  日期：1990.5
• 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.
• Nucleophilic substitution at nitrogen and carboxyl carbon of N-aryl-O-pivaloylhydroxylamines in aqueous solution: competition with SN1 solvolysis of model carcinogens
  作者：John S. Helmick、Michael Novak

  DOI：10.1021/jo00008a064

  日期：1991.4
• SN2 reactions of a carbon nucleophile with N-aryl-O-pivaloylhydroxylamines: a model for in vivo reactions of carcinogenic metabolites of aromatic amines
  作者：Michael Novak、Kristy A. Martin、Julie L. Heinrich

  DOI：10.1021/jo00284a012

  日期：1989.11