O-benzoyl-N-phenyl-acetohydroxamic acid | 27125-80-0

• 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: O-benzoyl-N-phenyl-acetohydroxamic acid
• 英文别名: N-(benzoyloxy)-N-phenylacetamide；N-benzoyloxy-N-phenylacetamide；(N-acetylanilino) benzoate
• CAS: 27125-80-0
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: DHFAXANGRMKOGX-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C (polymorph)
• 沸点：
  368.6±25.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-benzoyl-N-phenyl-acetohydroxamic acid 在 水 作用下， 以 甲醇 为溶剂， 反应 0.83h， 生成 N-乙酰苯胺 、 苯甲酸
  参考文献：
  名称：

  Photoacid generators (PAGs) based on N-acyl-N-phenylhydroxylamines for carboxylic and sulfonic acids

  摘要：

  Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-acyl-N-phenylhydroxylamines have been demonstrated. Irradiation of o-carboxylates and thermally rearranged o-arenesulfonates of N-acyl-N-phenylhydroxylamines using UV light (>= 254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of N-acyl-N-phenylhydroxylamines was found to be dependent on their N-acyl substituents. Further, polymer bearing o-arenesulfonates of N-acyl-N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.049
• 作为产物：
  描述：

  苯基羟胺 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.08h， 生成 O-benzoyl-N-phenyl-acetohydroxamic acid
  参考文献：
  名称：

  Photoacid generators (PAGs) based on N-acyl-N-phenylhydroxylamines for carboxylic and sulfonic acids

  摘要：

  Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-acyl-N-phenylhydroxylamines have been demonstrated. Irradiation of o-carboxylates and thermally rearranged o-arenesulfonates of N-acyl-N-phenylhydroxylamines using UV light (>= 254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of N-acyl-N-phenylhydroxylamines was found to be dependent on their N-acyl substituents. Further, polymer bearing o-arenesulfonates of N-acyl-N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.049

文献信息

• Mode of action of carcinogenic amines. Part I. Oxidation of N-arylhydroxamic acids
  作者：A. R. Forrester、M. M. Ogilvy、R. H. Thomson

  DOI：10.1039/j39700001081

  日期：——

  Oxidation of N-arylhydroxamic acids in benzene with silver oxide gave the corresponding aryl nitroso-compounds, NO-diacylarylhydroxylamines, aryl nitro-compounds, and amides. The first two types of product are considered to arise by an intermolecular electrophilic acylation reaction and the other two by a homolytic oxygen-transfer process.

  用氧化银氧化苯中的N-芳基异羟肟酸，得到相应的芳基亚硝基化合物，NO-二酰基芳基羟胺，芳基硝基化合物和酰胺。认为前两种产物是通过分子间亲电酰化反应产生的，而另外两种是通过均相氧转移过程产生的。
• Reactions of 2-acylthiazolium salts with N-arylhydroxylamines
  作者：Luísa M Ferreira、Ana M Lobo、Sundaresan Prabhakar、Antonieta C Teixeira

  DOI：10.1016/s0040-4020(98)01161-2

  日期：1999.3

  2-Acylthiazolium salts, easily obtained by alkylation of the corresponding 2-acylthiazoles with methyl triflate, react with N-arylhydroxylamines to furnish the O-acyl derivatives of relevance in the induction of cancer by aromatic amines. (C) 1999 Elsevier Science Ltd. All rights reserved.
• NHC-Catalyzed <i>O</i>-Selective Addition of Nitrosoarenes with Aldehydes
  作者：Gang Wang、Xia Chen、Yi Zhang、Weijun Yao、Cheng Ma

  DOI：10.1021/ol4012458

  日期：2013.6.21

  An NHC-catalyzed O-selective addition of nitrosoarenes with aldehydes probably upon a dual-activation mode was developed, generating a variety of O-acyl hydroxylamines without any detectable competing amidation byproducts.