N-methyl-2,2,2-trifluorothioacetamide | 65523-76-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N-methyl-2,2,2-trifluorothioacetamide
• 英文别名: 2,2,2-trifluoro-N-methylethanethioamide
• CAS: 65523-76-4
• 化学式: C₃H₄F₃NS
• mdl: MFCD19217875
• 分子量: 143.133
• InChiKey: ZAQYGDOTTVKHNU-UHFFFAOYSA-N

物化性质

• 沸点：
  74.3±45.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-2,2,2-trifluorothioacetamide 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到N-methyl-N-trifluorothioacetyl-acetamide
  参考文献：
  名称：

  Synthesis and Reactivity of Trifluorodithioacetates Derived from Trifluorothioacetamides

  摘要：

  A general synthesis of trifluorodithioacetates is described by thiolysis of trifluorothioamidium salts, derived from trifluorothioacetamides. The reactivity of these CF3 bearing C-2 building blocks has been investigated towards nucleophiles and in cycloaddition reactions. Trifluorodithioacetates react with dienes to give thiopyrans and with diazo compounds to give trifluoromethyl vinyl sulphides via thiirane intermediates. With amines, trifluorodithioacetates give rise to trifluorothioacetamides while thiols add by thiophilic attack leading to new trifluoroethane dithioacetal disulphide. Two equivalents of phosphite furnish one equivalent of thiophosphate and one of phosphorylated trifluoroethane.

  DOI：

  10.1002/prac.199733901128
• 作为产物：
  描述：

  N-甲基-2,2,2-三氟乙酰胺 在 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 以90%的产率得到N-methyl-2,2,2-trifluorothioacetamide
  参考文献：
  名称：

  Synthesis and Reactivity of Trifluorodithioacetates Derived from Trifluorothioacetamides

  摘要：

  A general synthesis of trifluorodithioacetates is described by thiolysis of trifluorothioamidium salts, derived from trifluorothioacetamides. The reactivity of these CF3 bearing C-2 building blocks has been investigated towards nucleophiles and in cycloaddition reactions. Trifluorodithioacetates react with dienes to give thiopyrans and with diazo compounds to give trifluoromethyl vinyl sulphides via thiirane intermediates. With amines, trifluorodithioacetates give rise to trifluorothioacetamides while thiols add by thiophilic attack leading to new trifluoroethane dithioacetal disulphide. Two equivalents of phosphite furnish one equivalent of thiophosphate and one of phosphorylated trifluoroethane.

  DOI：

  10.1002/prac.199733901128

文献信息

• Trifluoromethylation of heterocumulenes with trimethyl(trifluoromethyl)silane in the presence of fluoride ions: synthesis of trifluoroacetamides and trifluorothioacetamides from isocyanates and isothiocyanates
  作者：Nataliya V Kirij、Yurii L Yagupolskii、Nataliya V Petukh、Wieland Tyrra、Dieter Naumann

  DOI：10.1016/s0040-4039(01)01764-6

  日期：2001.11

  Trimethyl(trifluoromethyl)silane reacts in the presence of fluoride ions with isocyanates and isothiocyanates under mild conditions to give corresponding trifluoroacetamides and trifluorothioacetamides in high yields.

  三甲基（三氟甲基）硅烷在氟离子存在下与异氰酸酯和异硫氰酸酯在温和的条件下反应，以高收率得到相应的三氟乙酰胺和三氟硫代乙酰胺。
• Multi-step reactions of N-monosubstituted (polyfluoroalkane)thioamides with alkyllithium reagents
  作者：Sergiy S. Mikhailichenko、Alexander V. Rudnichenko、Vadim M. Timoshenko、Alexander N. Chernega、Yuriy G. Shermolovich、Fabienne Grellepois、Charles Portella

  DOI：10.1016/j.jfluchem.2007.02.007

  日期：2007.7

  Reactions of N-alkyl- or N-aryl(perfluoroalkyl)thiocarboxamides with alkyl lithium reagents are described. Trifluorothioacetamides are converted into the corresponding lithium salts. Compounds bearing a long polyfluorinated chain terminated by a CHF2 group and compounds containing an N-alkyl substituent with a proton adjacent to nitrogen react further via a multi-step reaction sequence involving HF

  描述了N-烷基-或N-芳基（全氟烷基）硫代羧酰胺与烷基锂试剂的反应。将三氟硫代乙酰胺转化为相应的锂盐。带有通过CHF 2基团终止的多氟长链的化合物和含有N-烷基取代基且质子与氮相邻的化合物进一步通过涉及HF消除，然后进行乙烯基氟取代和/或S N '型的多步反应序列进一步反应氟取代。这些转变导致不饱和的N-单取代的多氟代硫代酰胺。
• Synthesis and Reactivity of Trifluorodithioacetates Derived from Trifluorothioacetamides
  作者：Frédéric Laduron、Claire Nyns、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1002/prac.199733901128

  日期：——

  A general synthesis of trifluorodithioacetates is described by thiolysis of trifluorothioamidium salts, derived from trifluorothioacetamides. The reactivity of these CF3 bearing C-2 building blocks has been investigated towards nucleophiles and in cycloaddition reactions. Trifluorodithioacetates react with dienes to give thiopyrans and with diazo compounds to give trifluoromethyl vinyl sulphides via thiirane intermediates. With amines, trifluorodithioacetates give rise to trifluorothioacetamides while thiols add by thiophilic attack leading to new trifluoroethane dithioacetal disulphide. Two equivalents of phosphite furnish one equivalent of thiophosphate and one of phosphorylated trifluoroethane.