N-Butyl-N-nitro-2-methylpropanamide | 136805-92-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-Butyl-N-nitro-2-methylpropanamide
• 英文别名: N-butyl-2-methyl-N-nitropropanamide
• CAS: 136805-92-0
• 化学式: C₈H₁₆N₂O₃
• 分子量: 188.227
• InChiKey: LNFONZJAHGNDOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-butyl-2-methylpropanamide 在 morpholinium nitrate 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以98%的产率得到N-Butyl-N-nitro-2-methylpropanamide
  参考文献：
  名称：

  Improved methods for the N-nitration of amides

  摘要：

  The reactivity of several nitrating mixtures with amides has been compared. Ammonium nitrate/trifluoroacetic anhydride, morpholinium nitrate/trifluoroacetic anhydride, and morpholinium nitrate/heptafluorobutyric anhydride are the reagents of choice since, in CH2Cl2 at 0-degrees-C, they give N-alkyl-N-nitrocarboxamides and N-nitrolactams in excellent yields. Mechanistic details of these nitrations have been elucidated. Trifluoroacetyl nitrate, which arises from the reaction R2NH2+NO3- + 2(CF3CO)2O --> CF3COONO2 + CF3CONR2 + 2CF3COOH, appears to cause the direct N-nitration of carboxamides.

  DOI：

  10.1021/jo00025a017

文献信息

• Improved methods for the N-nitration of amides
  作者：Pedro Romea、Montse Aragones、Jordi Garcia、Jaume Vilarrasa

  DOI：10.1021/jo00025a017

  日期：1991.12

  The reactivity of several nitrating mixtures with amides has been compared. Ammonium nitrate/trifluoroacetic anhydride, morpholinium nitrate/trifluoroacetic anhydride, and morpholinium nitrate/heptafluorobutyric anhydride are the reagents of choice since, in CH2Cl2 at 0-degrees-C, they give N-alkyl-N-nitrocarboxamides and N-nitrolactams in excellent yields. Mechanistic details of these nitrations have been elucidated. Trifluoroacetyl nitrate, which arises from the reaction R2NH2+NO3- + 2(CF3CO)2O --> CF3COONO2 + CF3CONR2 + 2CF3COOH, appears to cause the direct N-nitration of carboxamides.