N-(triflyloxy)-N-methylfurancarboxamide | 156025-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N-(triflyloxy)-N-methylfurancarboxamide
• 英文别名: (Furan-2-carbonyl-methylamino) trifluoromethanesulfonate；[furan-2-carbonyl(methyl)amino] trifluoromethanesulfonate
• CAS: 156025-78-4
• 化学式: C₇H₆F₃NO₅S
• 分子量: 273.19
• InChiKey: HMFVVDWXONXNPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(triflyloxy)-N-methylfurancarboxamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-isopropoxymethyl-N-benzyl-2-furancarboxamide
  参考文献：
  名称：

  A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides

  摘要：

  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.

  DOI：

  10.1021/jo00092a007
• 作为产物：
  描述：

  呋喃甲酰氯 在 2,6-二甲基吡啶 、 氢氧化钾 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 N-(triflyloxy)-N-methylfurancarboxamide
  参考文献：
  名称：

  A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides

  摘要：

  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.

  DOI：

  10.1021/jo00092a007

文献信息

• 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：——
• 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.