N-hydroxy-2-o-tolylacetamide | 2594-02-7

• 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: N-hydroxy-2-o-tolylacetamide
• 英文别名: o-Tolyl-acethydroxamsaeure；N-hydroxy-2-(2-methylphenyl)acetamide
• CAS: 2594-02-7
• 化学式: C₉H₁₁NO₂
• mdl: MFCD09928811
• 分子量: 165.192
• InChiKey: LHZYGVQTVOOQJB-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  邻甲基苯乙酸 、 N-hydroxy-2-o-tolylacetamide 以 四氢呋喃 为溶剂， 反应 15.0h， 以78%的产率得到2-o-tolyl-N-(2-o-tolylacetoxy)acetamide
  参考文献：
  名称：

  Synthesis of Hydroxamic Acids by Activation of Carboxylic Acids withN,N′-Carbonyldiimidazole: Exploring the Efficiency of the Method

  摘要：

  Activation of carboxylic acids with N,N'-carbonyldiimidazole followed by the reaction with anhydrous or aqueous hydroxylamine hydrochloride was demonstrated to be an operationally simple method for the synthesis of hydroxamic acids in good yield and high purity after aqueous workup. The potential by-product, N,O-diacylhydroxylamine, is cleanly transformed to hydroxamic acid in these reaction conditions.

  DOI：

  10.1080/00397910903026723
• 作为产物：
  描述：

  邻甲基苯乙酸 在 N,N'-羰基二咪唑 、 盐酸羟胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 以99%的产率得到N-hydroxy-2-o-tolylacetamide
  参考文献：
  名称：

  Synthesis of Hydroxamic Acids by Activation of Carboxylic Acids withN,N′-Carbonyldiimidazole: Exploring the Efficiency of the Method

  摘要：

  Activation of carboxylic acids with N,N'-carbonyldiimidazole followed by the reaction with anhydrous or aqueous hydroxylamine hydrochloride was demonstrated to be an operationally simple method for the synthesis of hydroxamic acids in good yield and high purity after aqueous workup. The potential by-product, N,O-diacylhydroxylamine, is cleanly transformed to hydroxamic acid in these reaction conditions.

  DOI：

  10.1080/00397910903026723

文献信息

• Synthesis of Hydroxamic Acids by Using the Acid Labile O-2-Methylprenyl Protecting Group
  作者：Aigars Jirgensons、Anna Nikitjuka

  DOI：10.1055/s-0032-1317687

  日期：——

  Coupling of carboxylic acids with O-2-methylprenyl hydroxylamine provided O-protected hydroxamic acids, which could be deprotected by treatment with trifluoroacetic acid (TFA) in dichloromethane giving volatile by-products. Protected hydroxamic acids could be N-arylated or alkylated followed by deprotection to give N-substituted hydroxamic acids.

  羧酸与 O-2-甲基异戊二烯羟胺的偶联提供了 O-保护的异羟肟酸，可以通过在二氯甲烷中用三氟乙酸 (TFA) 处理来脱保护，产生挥发性副产物。受保护的异羟肟酸可以被 N-芳基化或烷基化，然后去保护以得到 N-取代的异羟肟酸。
• Synthesis of Hydroxamic Acids by Activation of Carboxylic Acids with<i>N</i>,<i>N</i>′-Carbonyldiimidazole: Exploring the Efficiency of the Method
  作者：Natalija Usachova、Gundars Leitis、Aigars Jirgensons、Ivars Kalvinsh

  DOI：10.1080/00397910903026723

  日期：2010.2.26

  Activation of carboxylic acids with N,N'-carbonyldiimidazole followed by the reaction with anhydrous or aqueous hydroxylamine hydrochloride was demonstrated to be an operationally simple method for the synthesis of hydroxamic acids in good yield and high purity after aqueous workup. The potential by-product, N,O-diacylhydroxylamine, is cleanly transformed to hydroxamic acid in these reaction conditions.