N-[(trifluoromethylsulfonyl)aminomethyl]acetamide

• 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-[(trifluoromethylsulfonyl)aminomethyl]acetamide
• 英文别名: N-({[(trifluoromethyl)sulfonyl]amino}methyl)acetamide；N-[(trifluoromethylsulfonylamino)methyl]acetamide
• 化学式: C₄H₇F₃N₂O₃S
• mdl: MFCD06616935
• 分子量: 220.172
• InChiKey: MDOTXFWDJXCEEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(trifluoromethylsulfonyl)aminomethyl]acetamide 、 聚合甲醛 在 硫酸 作用下， 生成 3,5-bis(trifluoromethylsulfonyl)tetrahydro-1,3,5-oxadiazine
  参考文献：
  名称：

  Triflamidomethyl and oxymethyl derivatives of 1,2,3-triazoles

  摘要：

  The reactions of some 1,2,3-triazoles with formaldehyde and triflamide have been studied. N-(Hydroxy-methyl)-2-phenyl-2H-1,2,3-triazole-4-carboxamide reacts with triflamide in sulfuric acid to afford 2-phenyl-2H-1,2,3-triazole-4-carboxamide, bis(triflamido)methane, and N,N-bis[(trifluoromethylsulfonyl)aminomethyl]-triflamide. In the presence of K2CO3 4-amino-5-nitro-2-ethyl-1,2,3-triazole is reduced with hydrazine hydrate to 2-ethyl-2De-1,2,3-triazole-4,5-diamine, and with formaldehyde in the presence of K2CO3 it gives N,N-bis(2-ethyl-5-nitro-2De-1,2,3-triaxol-4-yl)methanediamine, which reacts with paraformaldehyde under acidic conditions with the formation of 4-aminomethyl-5-nitro-2-ethyl-1,2,3-triazole.

  DOI：

  10.1134/s1070363215100163
• 作为产物：
  描述：

  聚合甲醛 、 三氟甲磺酰胺 、 乙腈 以 磷酸 为溶剂， 反应 4.0h， 以36%的产率得到N-[(trifluoromethylsulfonyl)aminomethyl]acetamide
  参考文献：
  名称：

  Cascade Transformations of Trifluoromethanesulfonamide in Reaction with Formaldehyde

  摘要：

  三氟甲磺酰胺在酸性介质中与多聚甲醛反应，生成开链和环状缩合产物：双(三氟甲磺酰氨基)甲烷、N, N-双(三氟甲磺酰氨基甲基)三氟甲烷磺酰胺、5-(三氟甲磺酰基)二氢-1,3,5-二恶嗪、3,5-双(三氟甲磺酰基)四氢-1、1,3,5-三(三氟甲基磺酰基)六氢-1,3,5-三嗪、5,7-双(三氟甲基磺酰基)-1,3,5,7-二噁二唑烷和 5,7,9-三(三氟甲基磺酰基)-1,3,5,7,9-二噁三嗪。乙腈在三氟甲磺酰胺-甲醛-磷酸体系中进行氨基烷基化反应，可生成 N-(三氟甲基磺酰氨基甲基)乙酰胺。

  DOI：

  10.1007/s11178-005-0351-3

文献信息

• Cascade Transformations of Trifluoromethanesulfonamide in Reaction with Formaldehyde
  作者：V. I. Meshcheryakov、A. I. Albanov、B. A. Shainyan

  DOI：10.1007/s11178-005-0351-3

  日期：2005.9

  Trifluoromethanesulfonamide reacts with paraformaldehyde in acid medium to give both open-chain and cyclic condensation products: bis(trifluoromethylsulfonylamino)methane, N, N-bis(trifluoromethylsulfonylaminomethyl)trifluoromethanesulfonamide, 5-(trifluoromethylsulfonyl)dihydro-1,3,5-dioxazine, 3,5-bis(trifluoromethylsulfonyl)tetrahydro-1,3,5-oxadiazine, 1,3,5-tris(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, 5,7-bis(trifluoromethylsulfonyl)-1,3,5,7-dioxadiazocane, and 5,7,9-tris(trifluoromethylsulfonyl)-1,3,5,7,9-dioxatriazecane. Amidoalkylation of acetonitrile in the system trifluoromethanesulfonamide-paraformaldehyde-phosphoric acid leads to formation of N-(trifluoromethylsulfonylaminomethyl)acetamide.

  三氟甲磺酰胺在酸性介质中与多聚甲醛反应，生成开链和环状缩合产物：双(三氟甲磺酰氨基)甲烷、N, N-双(三氟甲磺酰氨基甲基)三氟甲烷磺酰胺、5-(三氟甲磺酰基)二氢-1,3,5-二恶嗪、3,5-双(三氟甲磺酰基)四氢-1、1,3,5-三(三氟甲基磺酰基)六氢-1,3,5-三嗪、5,7-双(三氟甲基磺酰基)-1,3,5,7-二噁二唑烷和 5,7,9-三(三氟甲基磺酰基)-1,3,5,7,9-二噁三嗪。乙腈在三氟甲磺酰胺-甲醛-磷酸体系中进行氨基烷基化反应，可生成 N-(三氟甲基磺酰氨基甲基)乙酰胺。
• Triflamidomethyl and oxymethyl derivatives of 1,2,3-triazoles
  作者：B. A. Shainyan、V. I. Meshcheryakov

  DOI：10.1134/s1070363215100163

  日期：2015.10

  The reactions of some 1,2,3-triazoles with formaldehyde and triflamide have been studied. N-(Hydroxy-methyl)-2-phenyl-2H-1,2,3-triazole-4-carboxamide reacts with triflamide in sulfuric acid to afford 2-phenyl-2H-1,2,3-triazole-4-carboxamide, bis(triflamido)methane, and N,N-bis[(trifluoromethylsulfonyl)aminomethyl]-triflamide. In the presence of K2CO3 4-amino-5-nitro-2-ethyl-1,2,3-triazole is reduced with hydrazine hydrate to 2-ethyl-2De-1,2,3-triazole-4,5-diamine, and with formaldehyde in the presence of K2CO3 it gives N,N-bis(2-ethyl-5-nitro-2De-1,2,3-triaxol-4-yl)methanediamine, which reacts with paraformaldehyde under acidic conditions with the formation of 4-aminomethyl-5-nitro-2-ethyl-1,2,3-triazole.
• Structure and intramolecular hydrogen bonds in Bis(trifluoromethylsulfonylamino)methane and N-[(trifluoromethylsulfonyl)aminomethyl]acetamide
  作者：I. V. Sterkhova、V. I. Mescheryakov、N. N. Chipanina、V. A. Kuhareva、T. N. Aksamentova、V. K. Turchaninov、B. A. Shainyan

  DOI：10.1134/s1070363206040165

  日期：2006.4

  Bis(trifluoromethylsulfonylamino)methane in an inert medium exists as an equilibrium mixture of monomeric forms with various types of intramolecular hydrogen bonds, whose population depends on the polarity of the medium. The energetically most favorable form is a symmetrical form containing two N-(HO)-O-...=S bonds. Less stable are the isomer with two N-(HF)-F-...-C bonds and the unsymmetrical isomer with two different hydrogen bonds. N-[(Trifluoromethylsulfonyl)aminomethyl]acetamide contains one intramolecular intramolecular N-(HO)-O-...=C hydrogen bond and preserves ability for self-association.