N-phenyl-α,α-dichloroacetohydroxamic acid | 34282-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phenyl-α,α-dichloroacetohydroxamic acid
• 英文别名: 2,2-dichloro-N-hydroxy-N-phenylacetamide
• CAS: 34282-44-5
• 化学式: C₈H₇Cl₂NO₂
• 分子量: 220.055
• InChiKey: LXZPHFYNONJWFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-α,α-dichloroacetohydroxamic acid 在 苯基溴化硒 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以1.4 g的产率得到2,2-dichloro-N-(4-hydroxyphenyl)acetamide
  参考文献：
  名称：

  Redox‐Neutral Selenium‐Catalysed Isomerisation of para ‐Hydroxamic Acids into para ‐Aminophenols

  摘要：

  AbstractA selenium‐catalysed para‐hydroxylation of N‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para‐hydroxyaniline derivatives. The mechanism is studied through both 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols.

  DOI：

  10.1002/anie.202100801
• 作为产物：
  描述：

  硝基苯 在 rhodium on carbon 、 碳酸氢钠 、 一水合肼 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.0h， 生成 N-phenyl-α,α-dichloroacetohydroxamic acid
  参考文献：
  名称：

  Redox‐Neutral Selenium‐Catalysed Isomerisation of para ‐Hydroxamic Acids into para ‐Aminophenols

  摘要：

  AbstractA selenium‐catalysed para‐hydroxylation of N‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para‐hydroxyaniline derivatives. The mechanism is studied through both 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols.

  DOI：

  10.1002/anie.202100801

文献信息

• Quantitation of N-(2-hydroxy-4-methoxyphenyl)glyoxylhydroxamic acid, a reactive intermediate in reactions of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one
  作者：Sylvia V. Copaja、Hector R. Bravo、Hermann M. Niemeyer

  DOI：10.1021/jo00368a029

  日期：1986.9
• Redox‐Neutral Selenium‐Catalysed Isomerisation of <i>para</i> ‐Hydroxamic Acids into <i>para</i> ‐Aminophenols
  作者：Hsiang‐Yu Chuang、Manuel Schupp、Ricardo Meyrelles、Boris Maryasin、Nuno Maulide

  DOI：10.1002/anie.202100801

  日期：2021.6.14

  AbstractA selenium‐catalysed para‐hydroxylation of N‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para‐hydroxyaniline derivatives. The mechanism is studied through both 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols.