N-(triflyloxy)-N-methylbenzamide | 156025-77-3

• 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-(triflyloxy)-N-methylbenzamide
• 英文别名: [Benzoyl(methyl)amino] trifluoromethanesulfonate
• CAS: 156025-77-3
• 化学式: C₉H₈F₃NO₄S
• 分子量: 283.228
• InChiKey: CUSXXRSCOFJJSK-UHFFFAOYSA-N

物化性质

• 沸点：
  289.8±50.0 °C(Predicted)
• 密度：
  1.502±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N-(triflyloxy)-N-methylbenzamide 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-phenyl-5,6-dihydro-4H-1,3-oxazine
  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：

  苯甲酰氯 在 2,6-二甲基吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 N-(triflyloxy)-N-methylbenzamide
  参考文献：
  名称：

  酰胺氮中心的 SN2 反应可实现酰肼的合成

  摘要：

  通过在亲电酰胺与亲核胺上采用 S N 2 策略，公开了一种用于实际合成酰肼的新 NN 偶联方法。该反应条件温和、底物范围广、官能团耐受性好、易于扩展，适用于多种已批准药物分子的后期修饰，从而实现复杂酰肼支架的合成。

  DOI：

  10.1002/anie.202317570

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.
• S_N2 Reaction at the Amide Nitrogen Center Enables Hydrazide Synthesis
  作者：Wen Fang、Zhi‐Wen Luo、Ye‐Cheng Wang、Wei Zhou、Lei Li、Yimin Chen、Xiangke Zhang、Mingji Dai、Jian‐Jun Dai

  DOI：10.1002/anie.202317570

  日期：2024.4.2

  to the practical synthesis of hydrazides is disclosed by employing an SN2 strategy at electrophilic amides with nucleophilic amines. The reaction exhibits mild conditions, broad substrate scope, excellent functional group tolerance, easy scalability, and is applicable to the late-stage modification of various approved drug molecules, thus enabling complex hydrazide scaffold synthesis.

  通过在亲电酰胺与亲核胺上采用 S N 2 策略，公开了一种用于实际合成酰肼的新 NN 偶联方法。该反应条件温和、底物范围广、官能团耐受性好、易于扩展，适用于多种已批准药物分子的后期修饰，从而实现复杂酰肼支架的合成。