N-Hydroxy-N-methylbut-3-enamide | 143217-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Hydroxy-N-methylbut-3-enamide
• 英文别名: N-hydroxy-N-methyl-3-butenamide
• CAS: 143217-21-4
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: YQDAYHGWVQZZOA-UHFFFAOYSA-N

物化性质

• 沸点：
  184.6±33.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Hydroxy-N-methylbut-3-enamide 在 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-methyl-2-bromo-3-butenamide
  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：

  丁-3-烯酰氯 、 N-甲基羟胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以55%的产率得到N-Hydroxy-N-methylbut-3-enamide
  参考文献：
  名称：

  N-烷基-O-酰基异羟肟酸的碱催化重排：2-酰氧基酰胺的合成

  摘要：

  活化的N-烷基-O-酰基异羟肟酸衍生物21a–t经过热催化和碱催化重排，以良好的产率（50–100％）得到2-酰氧基酰胺22a–t。筛选了一系列无机和有机碱以介导重排21至22的效率，但是，发现简单的有机碱（例如Et 3 N）是最有效的。在该反应中，芳族和脂族衍生的O-酰基均被耐受。发现O-酰基的电子性质会影响吸电子基团的重排速率（21l和21o）增加了观察速率，而给电子基团（21m和21n）降低了观察速率。与21a和21h的交叉实验表明了涉及游离酰氧基阴离子中间体的机理。容易浮雕的要求质子 毗邻 羰基 的 酰胺由于在所研究的反应条件下21r和21t均不能重排，因此发现对于重排是必要的。

  DOI：

  10.1039/a909903d

文献信息

• A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides
  作者：Robert V. Hoffman、Naresh K. Nayyar

  DOI：10.1021/jo00092a007

  日期：1994.7

  A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1-isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide structural diversity can be generated easily from N-(1-isopropoxyalkyl) amides available by this methodology.
• Generation of N-acyl iminium ions from ionization-rearrangement reactions of N-triflyloxy amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Jean M. Shankweiler、Bruce W. Klinekole

  DOI：10.1016/s0040-4039(00)76872-9

  日期：1994.5

  N-Triflyloxy amides undergo ionization in refluxing isopropanol to give N-acyliminium ions which can be trapped by addition of allyltrimethylsilane to the reaction mixture. Alternatively they can be converted to N-(isopropoxy)alkyl amides and then back to N-acyliminium ions under a variety of conditions.
• Hoffman Robert V., Nayyar Naresh K., J. Org. Chem, 59 (1994) N 13, S 3530-3539
  作者：Hoffman Robert V., Nayyar Naresh K.

  DOI：——

  日期：——
• Hoffman Robert V., Nayyar Naresh K., Shankweiler Jean M., Klinekole Bruce+, Tetrahedron Lett, 35 (1994) N 20, S 3231-3234
  作者：Hoffman Robert V., Nayyar Naresh K., Shankweiler Jean M., Klinekole Bruce+

  DOI：——

  日期：——
• 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.