N-(Mesyloxy)-N-methylphenylacetanilide | 142437-76-1

• 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-(Mesyloxy)-N-methylphenylacetanilide
• 英文别名: N-(mesyloxy)-N-methylphenylacetamide；[Methyl-(2-phenylacetyl)amino] methanesulfonate
• CAS: 142437-76-1
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: WOLIZBNCRKWDRN-UHFFFAOYSA-N

物化性质

• 沸点：
  359.8±35.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-methylphenylacetanilide 在 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到alpha-溴-N-甲基-2-苯乙酰胺
  参考文献：
  名称：

  Efficient conversion of O-sulfonylated arylacetohydroxamic acids to 2-substituted secondary amides

  摘要：

  DOI：

  10.1021/ja00041a064
• 作为产物：
  描述：

  N-甲基苯基乙酰氧肟酸 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到N-(Mesyloxy)-N-methylphenylacetanilide
  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
• Hoffman, Robert V.; Nayyar, Naresh K.; Chen, Wenting, Journal of the American Chemical Society, 1993, vol. 115, # 12, p. 5031 - 5034
  作者：Hoffman, Robert V.、Nayyar, Naresh K.、Chen, Wenting

  DOI：——

  日期：——
• Origins of Regioselectivity in the Reactions of .alpha.-Lactams with Nucleophiles
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00118a032

  日期：1995.6

  Regioselectivity in the reaction of alpha-lactams with nucleophiles results from two competing steps. Nucleophilic addition to the carbonyl group of the alpha-lactam, which yields rearranged, acyl-substituted products, is dependent on the nucleophilicity and the concentration of the nucleophile. Ring opening of the alpha-lactam to an ion pair intermediate, which gives nucleophile incorporation at C-2, is dependent on electronic effects of substituents at C-2. Groups which can stabilize positive charge at C-2 speed up ion pair formation, whereas electron-withdrawing groups slow the ring opening and give more carbonyl addition product. These factors are used to control the regioselectivity and produce a series of unsymmetric urea peptide mimetics in high yields and with complete regiochemical control.
• 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.
• 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.