N-(mesyloxy)-N-methyl(1-naphthyl)acetamide | 143217-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(mesyloxy)-N-methyl(1-naphthyl)acetamide
• 英文别名: [Methyl-(2-naphthalen-1-ylacetyl)amino] methanesulfonate
• CAS: 143217-07-6
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: PFVDHGFKCUZJBB-UHFFFAOYSA-N

物化性质

• 沸点：
  453.5±38.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(mesyloxy)-N-methyl(1-naphthyl)acetamide 在 sodium azide 、 15-冠醚-5 作用下， 以 二氯甲烷 为溶剂， 反应 45.0h， 以80%的产率得到N-Methyl-2-azido-2-(1-naphthyl)ethanamide
  参考文献：
  名称：

  Synthesis of .alpha.-azido and .alpha.-amino amides from N-[(methylsulfonyl)oxy]amides

  摘要：

  Effective new syntheses of 2-azido amides and 2-amino amides from N-(mesyloxy) amides 1 have been developed. 2-Azido amides are produced by treating 1 with sodium azide in the presence of 15-crown-5. 2-Amino amides result from the reaction of 1 with various amines. Regiochemical control in the preparation of 2-amino amides is possible by modulating the amine nucleophilicity by steric bulk.

  DOI：

  10.1021/jo00061a004
• 作为产物：
  描述：

  萘-1-基乙酰氯 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(mesyloxy)-N-methyl(1-naphthyl)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

• Preparation of .alpha.-Alkoxy Amides and .alpha.-Hydrazino Amides by Base-Promoted Reactions of N-Sulfonyloxy Amides
  作者：Robert V. Hoffman、Naresh K. Nayyar

  DOI：10.1021/jo00126a072

  日期：1995.10
• 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.
• Synthesis of .alpha.-azido and .alpha.-amino amides from N-[(methylsulfonyl)oxy]amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00061a004

  日期：1993.4

  Effective new syntheses of 2-azido amides and 2-amino amides from N-(mesyloxy) amides 1 have been developed. 2-Azido amides are produced by treating 1 with sodium azide in the presence of 15-crown-5. 2-Amino amides result from the reaction of 1 with various amines. Regiochemical control in the preparation of 2-amino amides is possible by modulating the amine nucleophilicity by steric bulk.