N-(triflyloxy)-N-methyl-2-carbetoxyethanamide | 156025-84-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(triflyloxy)-N-methyl-2-carbetoxyethanamide
• 英文别名: Ethyl 3-(methyl-(trifluoromethylsulfonyloxy)amino)-3-oxopropanoate；ethyl 3-[methyl(trifluoromethylsulfonyloxy)amino]-3-oxopropanoate
• CAS: 156025-84-2
• 化学式: C₇H₁₀F₃NO₆S
• 分子量: 293.221
• InChiKey: MFISMWJFVJHAFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(triflyloxy)-N-methyl-2-carbetoxyethanamide 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 N-(3-butenyl)-2-carbethoxyethanamide
  参考文献：
  名称：

  Generation of N-acyl iminium ions from ionization-rearrangement reactions of N-triflyloxy amides

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)76872-9
• 作为产物：
  描述：

  三氟甲磺酸酐 、 N-hydroxy-N-methyl-2-carbetoxyethanamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-(triflyloxy)-N-methyl-2-carbetoxyethanamide
  参考文献：
  名称：

  Generation of N-acyl iminium ions from ionization-rearrangement reactions of N-triflyloxy amides

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)76872-9

文献信息

• 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：——
• 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.