bis(trifluoromethanesulfonylamino)methane | 887603-01-2

• 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: bis(trifluoromethanesulfonylamino)methane
• 英文别名: bis(trifluoromethylsulfonylamino)methane；1,1,1-trifluoro-N-[(trifluoromethylsulfonylamino)methyl]methanesulfonamide
• CAS: 887603-01-2
• 化学式: C₃H₄F₆N₂O₄S₂
• 分子量: 310.198
• InChiKey: HNWQZUINYWBPMR-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C (decomp)(Solv: benzene (71-43-2))
• 沸点：
  252.4±50.0 °C(Predicted)
• 密度：
  1.818±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis(trifluoromethanesulfonylamino)methane 在 次氯酸叔丁酯 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以77%的产率得到N,N'-bis(trifluoromethylsulfonyl)urea
  参考文献：
  名称：

  Reaction of N,N′-Methylenebis(trifluoromethanesulfonamide) with Styrene under Oxidative Conditions

  摘要：

  The reaction of N,N '-methylenebis(trifluoromethanesulfonamide) with styrene in the oxidative system t-BuOCl/NaI affords triflamide, 2-iodo-1-phenylethanol, N,N '-bis(trifluoromethanesulfonyl)urea, and the product of styrene bistriflamidation. The mechanism is proposed involving hydrolysis and oxidation of the starting N,N '-methylenebis(trifluoromethanesulfonamide).

  DOI：

  10.1134/s1070428019050270
• 作为产物：
  描述：

  聚合甲醛 、 三氟甲磺酰胺 在 硫酸 作用下， 反应 1.0h， 以35%的产率得到bis(trifluoromethanesulfonylamino)methane
  参考文献：
  名称：

  Structure and intramolecular hydrogen bonds in Bis(trifluoromethylsulfonylamino)methane and N-[(trifluoromethylsulfonyl)aminomethyl]acetamide

  摘要：

  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.

  DOI：

  10.1134/s1070363206040165

文献信息

• Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde
  作者：M. Yu. Moskalik、V. I. Meshcheryakov、B. A. Shainyan

  DOI：10.1134/s1070428009110116

  日期：2009.11

  CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.

  三氟甲磺酰胺与低聚甲醛和琥珀酰胺的三组分缩合反应取决于反应条件，与双三氟甲烷磺酰胺基甲烷一起导致取代产物双[（三氟甲基磺酰基）氨基甲基]琥珀酰胺的形成，或环化产物N- [三氟甲基磺酰基]的形成氨基甲基]琥珀酰亚胺。通过三氟甲磺酰胺钠盐CF 3 SO 2 NHNa与N-氯甲基琥珀酰亚胺的反应来获得后者的尝试出乎意料地导致了N，N-双（琥珀酰亚胺基甲基）-三氟甲磺酰胺。类似地，CF 3 SO 2 NHNa与N的反应-氯甲基-邻苯二甲酰亚胺得到N，N-双（邻苯二甲酰亚胺基甲基）三氟甲磺酰胺。CF 3 SO 2 NHNa与琥珀酰亚胺和邻苯二甲酰亚胺在水和醇溶液中的反应导致开环并进一步转化形成的琥珀酸和邻苯二甲酸的单取代N-（三氟甲基磺酰基）酰胺。
• Condensation of Trifluoromethanesulfonamide with Paraformaldehyde and Oxamide
  作者：V. I. Meshcheryakov、M. Yu. Moskalik、I. Starke、B. A. Shainyan

  DOI：10.1134/s1070428010100052

  日期：2010.10

  Depending on the conditions, three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and oxamide led to the formation of linear products, N-mono- and N,N’-bis[(trifluoromethylsulfonyl)aminomethyl]oxamide, bis[(trifluoromethylsulfonyl)aminomethyl] ethanedioate, as well as of hydrolysis and cyclization product, N-(4,5-dioxo-1,3-oxazolidin-3-ylmethyl)trifluoromethanesulfonamide

  根据条件，三氟甲磺酰胺与多聚甲醛和草酰胺的三组分缩合导致线性产物N-单-和N，N'-双[（三氟甲基磺酰基）氨基甲基]乙酰胺，双[（三氟甲基磺酰基）氨基甲基]乙二酸酯以及水解和环化产物N-（4,5-dioxo-1,3-恶唑烷丁-3-基甲基）三氟甲磺酰胺。
• 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。
• 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.
• Spirocyclization in a three-component reaction of trifluoromethanesulfonamide with paraformaldehyde and malonamide
  作者：V. I. Meshcheryakova、B. A. Shainyan、V. E. Zavodnik、V. K. Bel’skii

  DOI：10.1134/s107042800608032x

  日期：2006.8