N,N'-bis(trifluoroacetyl)methanediamine | 176504-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: N,N'-bis(trifluoroacetyl)methanediamine
• 英文别名: N,N'-methylenebis(trifluoroacetamide)；2,2,2-trifluoro-N-[[(2,2,2-trifluoroacetyl)amino]methyl]acetamide
• CAS: 176504-61-3
• 化学式: C₅H₄F₆N₂O₂
• 分子量: 238.089
• InChiKey: JXODOXQNNFRGPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N,N'-bis(trifluoroacetyl)methanediamine 以 硫酸 为溶剂， 反应 3.0h， 以50%的产率得到N-(羟甲基)三氟乙酰胺
  参考文献：
  名称：

  Reactions of trifluoromethanesulfonamide with amides and paraformaldehyde

  摘要：

  Two- and three-component condensations of paraformaldehyde with trifluoromethanesulfonamide, acetamide, trifluoroacetamide, 1H-benzotriazole, methanesulfonamide, and malonamide were studied. N-Hydroxymethyl derivatives of trifluoroacetamide and 1H-benzotriazole reacted with trifluoromethanesulfonamide to give N-(trifluoroacetylaminomethyl)- and N-(1H-benzotriazol-1-ylmethyl)-substituted derivatives of tri-fluoromethanesulfonamide, as well as N,N'-methylenebis(trifluoromethylsulfonamide) and N-(trifluoromethyl-sulfonylaminomethyl)trifluoroacetamide as transamination products. Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and methanesulfonamide led to the formation of 1-methylsulfonyl-3,5-bis(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, and the reaction of trifluoromethanesulfonamide with paraformaldehyde and malonamide gave 4,10-bis(trifluoromethylsulfonyl)-2,4,8,10-tetraazaspiro-[5.5]undecane-1,7-dione whose structure was proved by X-ray analysis.

  DOI：

  10.1134/s1070428007060012
• 作为产物：
  描述：

  聚合甲醛 、 2,2,2-三氟乙酰胺 以 硫酸 为溶剂， 反应 3.0h， 以68%的产率得到N,N'-bis(trifluoroacetyl)methanediamine
  参考文献：
  名称：

  Reactions of trifluoromethanesulfonamide with amides and paraformaldehyde

  摘要：

  Two- and three-component condensations of paraformaldehyde with trifluoromethanesulfonamide, acetamide, trifluoroacetamide, 1H-benzotriazole, methanesulfonamide, and malonamide were studied. N-Hydroxymethyl derivatives of trifluoroacetamide and 1H-benzotriazole reacted with trifluoromethanesulfonamide to give N-(trifluoroacetylaminomethyl)- and N-(1H-benzotriazol-1-ylmethyl)-substituted derivatives of tri-fluoromethanesulfonamide, as well as N,N'-methylenebis(trifluoromethylsulfonamide) and N-(trifluoromethyl-sulfonylaminomethyl)trifluoroacetamide as transamination products. Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and methanesulfonamide led to the formation of 1-methylsulfonyl-3,5-bis(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, and the reaction of trifluoromethanesulfonamide with paraformaldehyde and malonamide gave 4,10-bis(trifluoromethylsulfonyl)-2,4,8,10-tetraazaspiro-[5.5]undecane-1,7-dione whose structure was proved by X-ray analysis.

  DOI：

  10.1134/s1070428007060012

文献信息

• Haloarenes in the Duff reaction under high pressures
  作者：I. P. Sedishev、N. E. Agafonov、A. A. Kutin、V. M. Zhulin

  DOI：10.1007/bf00696718

  日期：1995.11

  Reactions of haloarenes with urotropine in CF3COOH at elevated temperatures and high pressures give the corresponding aromatic aldehydes and/or N-(haloarylmethyl)trifluoroacetamides. The yeilds of the products and their ratio depend on electronic properties of substituents in the aromatic ring. The reaction carried out in a mixture of CF3COOH and (CF3CO)(2)O affords only amides.
• ANDREWS, MARK A., CARBOHYDR. RES., 194,(1989) C. 1-19
  作者：ANDREWS, MARK A.

  DOI：——

  日期：——
• Reactions of trifluoromethanesulfonamide with amides and paraformaldehyde
  作者：V. I. Meshcheryakov、Yu. S. Danilevich、M. Yu. Moskalik、N. Yu. Stetsyura、V. E. Zavodnik、V. K. Bel’skii、B. A. Shainyan

  DOI：10.1134/s1070428007060012

  日期：2007.6

  Two- and three-component condensations of paraformaldehyde with trifluoromethanesulfonamide, acetamide, trifluoroacetamide, 1H-benzotriazole, methanesulfonamide, and malonamide were studied. N-Hydroxymethyl derivatives of trifluoroacetamide and 1H-benzotriazole reacted with trifluoromethanesulfonamide to give N-(trifluoroacetylaminomethyl)- and N-(1H-benzotriazol-1-ylmethyl)-substituted derivatives of tri-fluoromethanesulfonamide, as well as N,N'-methylenebis(trifluoromethylsulfonamide) and N-(trifluoromethyl-sulfonylaminomethyl)trifluoroacetamide as transamination products. Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and methanesulfonamide led to the formation of 1-methylsulfonyl-3,5-bis(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, and the reaction of trifluoromethanesulfonamide with paraformaldehyde and malonamide gave 4,10-bis(trifluoromethylsulfonyl)-2,4,8,10-tetraazaspiro-[5.5]undecane-1,7-dione whose structure was proved by X-ray analysis.