2,2,3,3-tetrafluoropropanethioamide | 868546-77-4

• 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: 2,2,3,3-tetrafluoropropanethioamide
• 英文别名: 2,2,3,3-tetrafluorothiopropionamide
• CAS: 868546-77-4
• 化学式: C₃H₃F₄NS
• 分子量: 161.123
• InChiKey: PHRZGCWZFAXCFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  45-50 °C(Press: 0.07 Torr)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,3,3-tetrafluoropropanethioamide 在 次氯酸叔丁酯 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以54%的产率得到3,5-bis(2,2,3,3-tetrafluoroethyl)-1,2,4-thiadiazole
  参考文献：
  名称：

  1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

  摘要：

  1,1-Dichloropolfluoroalkanesulfenyl chlorides 与氨反应生成 1,1-Dichloropolfluoroalkanesulfenamides，在三乙胺的作用下转化为 3,5-双聚氟烷基-1,2,4-噻二唑。

  DOI：

  10.1007/s11178-005-0155-5
• 作为产物：
  描述：

  2,2,3,3-四氟丙胺 在 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以40%的产率得到2,2,3,3-tetrafluoropropanethioamide
  参考文献：
  名称：

  1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

  摘要：

  1,1-Dichloropolfluoroalkanesulfenyl chlorides 与氨反应生成 1,1-Dichloropolfluoroalkanesulfenamides，在三乙胺的作用下转化为 3,5-双聚氟烷基-1,2,4-噻二唑。

  DOI：

  10.1007/s11178-005-0155-5

文献信息

• Primary polyfluoroalkanethioamides as mild thioacylating reagents for alkyl amines and α-amino acid esters
  作者：Nadiia V. Pikun、Sergiy S. Mykhaylychenko、Irine B. Kulik、Yuriy G. Shermolovich

  DOI：10.1016/j.jfluchem.2016.03.005

  日期：2016.5

  transamidation reactions of primary amides of polyfluoroalkanethiocarboxylic acids with alkyl amines. Thionation of 2,2,3,3-tetrafluorosuccinamide with P4S10 in the presence of hexamethyldisiloxane gave 3,3,4,4-tetrafluoropyrrolidine-2,5-dithione. The latter compound and primary polyfluoroalkanethioamides were shown to react with α-amino acid esters under mild conditions affording their new polyfluoroalkanethioyl

  通过多氟链烷硫基羧酸的伯酰胺与烷基胺的氨基转移反应，得到了新的氟化N-烷基硫代酰胺。在六甲基二硅氧烷的存在下，用P 4 S 10对2,2,3,3-四氟琥珀酰胺进行亚硫酰化，得到3,3,4,4-四氟吡咯烷-2,5-二硫酮。已显示出后者化合物和伯多氟链烷硫基酰胺与α-氨基酸酯在温和的条件下反应，得到了它们新的多氟链烷硫基酰衍生物。
• New Synthesis of 2‐Polyfluoroalkyl Substituted 1,4,5,6‐Tetrahydro‐pyrimidines and 4,5,6,7‐Tetrahydro‐1<i>H</i>‐1,3‐diazepines
  作者：Alexander V. Rudnichenko、Yuriy G. Shermolovich

  DOI：10.1080/00397910601039192

  日期：2007.2.1

  Abstract A new efficient method for the preparation of 2‐polyfluoroalkyl substituted 1,4,5,6‐tetrahydropyrimidines and 4,5,6,7‐tetrahydro‐1H‐1,3‐diazepines by the reaction of polyfluoroalkanethiocarboxylic acids amides and 1,3‐propylenediamine or 1,4‐buthylenediamine is presented.

  摘要 一种通过多氟烷硫代羧酸酰胺与 1, 2-多氟烷基取代的 1,4,5,6-四氢嘧啶和 4,5,6,7-四氢-1H-1,3-二氮杂卓类反应制备的新方法存在 3-丙二胺或 1,4-丁二胺。
• Synthesis of fluorine-containing 1,3-thiazine derivatives from primary polyfluoroalkanethioamides
  作者：Sergiy S. Mykhaylychenko、Nadiia V. Pikun、Eduard B. Rusanov、Yuriy G. Shermolovich

  DOI：10.1016/j.jfluchem.2014.09.006

  日期：2014.12

  New fluorine-containing 1,3-thiazine derivatives were obtained by the reactions of primary polyfluoroalkanethioamides with methyl vinyl ketone and ethyl acrylate in the presence of boron trifluoride etherate. The outcome of the reactions depends on the type of α,β-unsaturated carbonyl compound and the polyfluoroalkyl chain length. Hydrolysis of the obtained 1,3-thiazines leads to the formation of thioester

  新含氟-1,3-噻嗪衍生物通过初级polyfluoroalkanethioamides的具有在三氟化硼醚的存在下甲基乙烯基酮和乙基丙烯酸酯反应得到的。反应的结果依赖于α，β不饱和羰基化合物和多氟烷链长的类型。所获得的1，3-噻嗪的水解导致硫酯衍生物的形成。
• Acylation of primary polyfluoroalkanethioamides
  作者：Sergiy S. Mykhaylychenko、Nadiia V. Pikun、Yuriy G. Shermolovich

  DOI：10.1016/j.jfluchem.2012.05.008

  日期：2012.8

  The reaction conditions and the nature of acyl chloride strongly influence the outcome of the primary polyfluoroalkanethioamides acylation. Preparation of NH-acetyl polyfluoroalkanethioamides was achieved conducting the reactions in acetonitrile at -20 degrees C in the presence of pyridine. The reactions of polyfluoroalkanethioamides with 5-hydroperfluoropentanoyl chloride are efficient for the synthesis of NH-acyl derivatives when they were carried out in the absence of a base under heating at 100 degrees C. The obtained NH-acyl polyfluoroalkanethioamides enter into cycloaddition reactions with 2,3-dimethylbutadiene at room temperature. (C) 2012 Elsevier B.V. All rights reserved.
• The synthesis of fluorine-containing endothiopeptide analogs by the reaction of perfluorinated dithiocarboxylic acids amides with esters of α-amino acids and dipeptides
  作者：Nadiia V. Pikun、Sergiy S. Mykhaylychenko、Yuriy G. Shermolovich

  DOI：10.24820/ark.5550190.p010.305

  日期：——

  One of the main approaches to the change and increase of biological activity of pharmacologically important peptides is the incorporation of non-natural amino acids into their structure.(1) A new method for the synthesis of fluorinated endothiopeptide analogs, containing the thiocarbonyl groups and fluorine atoms in the main peptide chain, is described. The new method consists of thioacylation reactions of the esters of corresponding a-amino acids and dipeptides with amides of perfluorinated dithiocarboxylic acids.[GRAPHICS].