N-hydroxy-N-methyl(4-fluorophenyl)acetamide | 143217-17-8

• 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-N-methyl(4-fluorophenyl)acetamide
• 英文别名: 2-(4-fluorophenyl)-N-hydroxy-N-methylacetamide
• CAS: 143217-17-8
• 化学式: C₉H₁₀FNO₂
• 分子量: 183.182
• InChiKey: HLAWJWDSSGVJLK-UHFFFAOYSA-N

物化性质

• 沸点：
  306.2±44.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-hydroxy-N-methyl(4-fluorophenyl)acetamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-(mesyloxy)-N-methyl(4-fluorophenyl)acetamide
  参考文献：
  名称：

  Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides

  摘要：

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.

  DOI：

  10.1021/jo00047a024
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 对氟苯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到N-hydroxy-N-methyl(4-fluorophenyl)acetamide
  参考文献：
  名称：

  Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides

  摘要：

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.

  DOI：

  10.1021/jo00047a024

文献信息

• Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00047a024

  日期：1992.10

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.