N-(triflyloxy)-N-methyl-3-phenylpropanamide | 156025-82-0

• 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-3-phenylpropanamide
• 英文别名: [Methyl(3-phenylpropanoyl)amino] trifluoromethanesulfonate
• CAS: 156025-82-0
• 化学式: C₁₁H₁₂F₃NO₄S
• 分子量: 311.282
• InChiKey: FJTOQNKXSRORGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  异丙醇 、 N-(triflyloxy)-N-methyl-3-phenylpropanamide 反应 1.0h， 以78%的产率得到N-(isopropoxymethyl)-3-phenylpropanamide
  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：

  3-苯丙酰氯 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 N-(triflyloxy)-N-methyl-3-phenylpropanamide
  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

• 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：——
• 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.