benzyl trifluorodithioacetate | 192882-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl trifluorodithioacetate
• 英文别名: Trifluorodithioacetic acid benzyl ester；benzyl 2,2,2-trifluoroethanedithioate
• CAS: 192882-94-3
• 化学式: C₉H₇F₃S₂
• 分子量: 236.282
• InChiKey: WLAJGXUPCSSPIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 benzyl trifluorodithioacetate 反应 10.0h， 以75%的产率得到6-Benzylsulfanyl-3,4-dimethyl-6-(trifluoromethyl)-2,5-dihydrothiopyran
  参考文献：
  名称：

  Portella, Charles; Shermolovich, Yuri G.; Tschenn, Olivier, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 7, p. 697 - 702

  摘要：

  DOI：
• 作为产物：
  描述：

  苄基2,2,2-三氟乙基硫醚 在 磺酰氯 、 zinc sulfide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 benzyl trifluorodithioacetate
  参考文献：
  名称：

  Portella, Charles; Shermolovich, Yuri G.; Tschenn, Olivier, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 7, p. 697 - 702

  摘要：

  DOI：

文献信息

• Thiocarbonylthio compound and free radical polymerization employing the same
  申请人：Shih Chen Kuo

  公开号：US20060270867A1

  公开（公告）日：2006-11-30

  A thiocarbonylthio compound and free radical polymerization employing the same. The thiocarbonylthio compound is represented by formula (I) or (II): wherein Z can be independently perfluoroalkyl, alkyl, haloalkyl, aryl, alkylaryl, haloalkylaryl, arylalkyl, aminoalkyl, alkylamino, alkoxy, alkoxyaryl, alkylsulfonyl, alkylsulfonylaryl, dialkylphosphinyl, or dialkylphosphinothioyl; R 1 and R 2 can be each independently hydrogen, alkyl, aryl, alkylaryl, arylalkyl, aminoalkyl, alkylamino, alkoxy or alkoxyaryl; R 3 is alkyl, aryl, aminoalkyl, alkylamino, alkoxy or alkoxyaryl. Furthermore, R can also be alkyl, aryl, alkylaryl, arylalkyl, aminoalkyl, alkylamino, alkoxy, haloalkylaryl, alkylsilyl, alkylthio, alkylthioaryl, or substituent contaning CN, CO, COOH, COOCH 3 or heterocyclic moieties; and R 4 is perfluoroalkyl. The thiocarbonylthio compound can be used as a reversible chain transfer agent in a free radical polymerization to obtain a polymer with a controlled molecular weight and narrow polydispersity.

  一种硫代羰基硫化合物和利用该硫代羰基硫化合物进行自由基聚合的方法。该硫代羰基硫化合物由式(I)或(II)表示：其中Z可以独立地是全氟烷基、烷基、卤代烷基、芳基、烷基芳基、卤代烷基芳基、芳基烷基、氨基烷基、烷基氨基、烷氧基、烷氧基芳基、烷基磺酰基、烷基磺酰基芳基、二烷基膦基或二烷基磷硫酰基；R1和R2可以各自独立地是氢、烷基、芳基、烷基芳基、芳基烷基、氨基烷基、烷基氨基、烷氧基或烷氧基芳基；R3是烷基、芳基、氨基烷基、烷基氨基、烷氧基或烷氧基芳基。此外，R也可以是烷基、芳基、烷基芳基、芳基烷基、氨基烷基、烷基氨基、烷氧基、卤代烷基芳基、烷基硅基、烷基硫基、烷基硫基芳基，或含有CN、CO、COOH、COOCH3或杂环基团的取代基；R4是全氟烷基。该硫代羰基硫化合物可用作自由基聚合中可逆链转移剂，以获得具有受控分子量和窄聚分度的聚合物。
• Cycloaddition reactions of polyfluoroalkylthioncarboxylic acid derivatives with dimethyl acetylenedicarboxylate (DMAD)
  作者：A.V Rudnichenko、V.M Timoshenko、Yu.G Shermolovich

  DOI：10.1016/j.jfluchem.2003.11.009

  日期：2004.3

  Polyfluoroalkyldithiocarboxylates react with dimethyl acetylenedicarboxylate (DMAD) to give 2-polyfluoroalkyl-1,3-dithioles and/or 2-polyfluoroalkylidene-1,3-dithioles depending on the substituent at the thiolic sulfur atom and on the length of the polyfluoroalkyl chain. Amides of polyfluoroalkylthioncarboxylic acids with DMAD give 2-methoxy-2-polyfluoroalkyl-5-methoxycarbonylmethylene-thiazolidin-4-ones

  取决于硫代硫原子上的取代基和多氟烷基链的长度，多氟烷基二硫代羧酸盐与乙炔基二甲酸二甲酯（DMAD）反应生成2-聚氟烷基-1,3-二硫醇和/或2-聚氟亚烷基-1,3-二硫醇。多氟烷基硫代羧酸与DMAD的酰胺得到2-甲氧基-2-多氟烷基-5-甲氧基羰基亚甲基-噻唑烷-4-酮。
• 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.
• Fluorinated ketenedithioacetals. 5. A new synthesis of perfluoroketenedithioacetals from alkyl perfluoroalkanedithiocarboxylates
  作者：Charles Portella、Yuri Shermolovich

  DOI：10.1016/s0040-4039(97)00799-5

  日期：1997.6

  The title compounds were synthesized by reaction of organometallic reagents with alkyl perfluoroalkanedithiocarboxylates via a thiophilic attack and a subsequent elimination of the alpha-fluoride. (C) 1997 Published by Elsevier Science Ltd.
• THIOCARBONYLTHIO COMPOUND AND FREE RADICAL POLYMERIZATION EMPLOYING THE SAME
  申请人：Shih Kuo Chen

  公开号：US20100048844A1

  公开（公告）日：2010-02-25

  A thiocarbonylthio compound and free radical polymerization employing the same. The thiocarbonylthio compound is represented by formula (I) or (II): wherein Z can be independently perfluoroalkyl, alkyl, haloalkyl, aryl, alkylaryl, haloalkylaryl, arylalkyl, aminoalkyl, alkylamino, alkoxy, alkoxyaryl, alkylsulfonyl, alkylsulfonylaryl, dialkylphosphinyl, or dialkylphosphinothioyl; R 1 and R 2 can be each independently hydrogen, alkyl, aryl, alkylaryl, arylalkyl, aminoalkyl, alkylamino, alkoxy or alkoxyaryl; R 3 is alkyl, aryl, aminoalkyl, alkylamino, alkoxy or alkoxyaryl. Furthermore, R can also be alkyl, aryl, alkylaryl, arylalkyl, aminoalkyl, alkylamino, alkoxy, haloalkylaryl, alkylsilyl, alkylthio, alkylthioaryl, or substituent contaning CN, CO, COOH, COOCH 3 or heterocyclic moieties; and R 4 is perfluoroalkyl. The thiocarbonylthio compound can be used as a reversible chain transfer agent in a free radical polymerization to obtain a polymer with a controlled molecular weight and narrow polydispersity.