N-(mesyloxy)-N-tert-butylphenylacetamide | 143217-11-2

• 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-tert-butylphenylacetamide
• 英文别名: [Tert-butyl-(2-phenylacetyl)amino] methanesulfonate
• CAS: 143217-11-2
• 化学式: C₁₃H₁₉NO₄S
• 分子量: 285.364
• InChiKey: APQYIKRMVOZJFN-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±35.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-tert-butylphenylacetamide 在 三乙胺 作用下， 以 乙腈 为溶剂， 以80%的产率得到N-tert-butyl-2-hydroxy-2-phenylacetamide
  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：

  苯乙酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(mesyloxy)-N-tert-butylphenylacetamide
  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

• Origins of Regioselectivity in the Reactions of α-Lactams with Nucleophiles. Two Distinct Acid-Catalyzed Pathways Involving O- and N-Protonation
  作者：Robert V. Hoffman、Zhiqiang Zhao、Abran Costales、David Clarke

  DOI：10.1021/jo020246h

  日期：2002.7.1

  nucleophilic attack at the C-3 carbon and yields C-3 products. The mechanism thus developed is very useful for understanding the changes in rates and product distributions in the reactions of sterically stabilized alpha-lactams with nucleophiles. It can also be extrapolated to other alpha-lactams so that a more coherent picture of alpha-lactam reactivity can be developed.

  立体稳定的α-内酰胺通过两种不同的酸催化途径反应。氧的质子化导致酰基碳发生亲核攻击并产生C-2产物。氮的质子化导致C-3碳发生亲核攻击，并产生C-3产物。这样开发的机理对于理解空间稳定的α-内酰胺与亲核试剂反应中速率和产物分布的变化非常有用。也可以将其外推至其他α-内酰胺，以便可以开发出更连贯的α-内酰胺反应性图片。
• 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
• Efficient conversion of O-sulfonylated arylacetohydroxamic acids to 2-substituted secondary amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Bruce W. Klinekole

  DOI：10.1021/ja00041a064

  日期：1992.7
• 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.