2-chloro-3,3,4,4,5,5,6,6-octafluoro-1-cyclohexene-1-sulfenyl chloride | 75667-96-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-chloro-3,3,4,4,5,5,6,6-octafluoro-1-cyclohexene-1-sulfenyl chloride
• 英文别名: 2-chloroperfluoro-1-cyclohexenesulfenyl chloride-1；2-chloroperfluoro-1-cyclohexenylsulfenyl chloride；Chloroperfluoro-1-cyclohexene-1-sulfenyl chloride；(2-Chloro-3,3,4,4,5,5,6,6-octafluorocyclohexen-1-yl) thiohypochlorite
• CAS: 75667-96-8
• 化学式: C₆Cl₂F₈S
• 分子量: 327.025
• InChiKey: FNBQPDIZCLUDLA-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 25 Torr)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-chloro-3,3,4,4,5,5,6,6-octafluoro-1-cyclohexene-1-sulfenyl chloride 在 potassium cyanide 作用下， 以 水 为溶剂， 反应 0.33h， 生成 2-Chloroperfluoro-1-cyclohexene-1-thiocyanate
  参考文献：
  名称：

  A thiophilic pathway for the synthesis of perfluorinated ?,?-unsaturated thiocyanates

  摘要：

  DOI：

  10.1007/bf00957809
• 作为产物：
  描述：

  1-benzylthio-2-chloroperfluoro-1-cyclohexene 在 氯 作用下， 以61%的产率得到2-chloro-3,3,4,4,5,5,6,6-octafluoro-1-cyclohexene-1-sulfenyl chloride
  参考文献：
  名称：

  ?,?-unsaturated sulfenyl chlorides

  摘要：

  DOI：

  10.1007/bf00949957

文献信息

• Functionalization of alkenes by polyfluorinated α,β-unsaturated sulphenyl chlorides Dual reactivity of perfluoro-2-methyl-2-penten-3-yl sulphenyl chloride in reactions with activated olefins
  作者：V.Ya. Popkova、V.K. Osmanov、A.V. Borisov、B.I. Ugrak、I.V. Bodrikov

  DOI：10.1016/0022-1139(96)03425-2

  日期：1996.4

  A dual reactivity of perfluoro-2-methyl-2-penten-3-yl sulphenyl chloride (1) in reactions with alkenes is described. Whereas 1 interacts with 3,3-dimethyl-1-butene and styrene in nitromethane solution in the sulphenyl chloride form, reactions with olefins that have mobile hydrogen atoms in an allylic position (e.g. allyl- and p-methoxyallyl-benzenes) occur through the tautomeric thioketone form −2

  描述了全氟-2-甲基-2-戊烯-3-基亚磺酰氯（1）在与烯烃反应中的双重反应性。1在亚硝基氯形式的硝基甲烷溶液中与3,3-二甲基-1-丁烯和苯乙烯相互作用，而与在烯丙基位置具有可移动氢原子的烯烃（例如烯丙基和对甲氧基烯丙基苯）的反应则通过互变异构硫酮形成-2-氯全氟-2-甲基戊硫酮-3（3）-通过烯重排形成产物。Chlorotropism在系统1 ⇌ 3中的亲核溶剂或催化剂的存在下负责的双重反应性1在上述反应。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.2, 6.2.1.6.4.2, page 117 - 172
  作者：

  DOI：——

  日期：——
• ?,?-unsaturated fluorine-containing thiocyanates
  作者：V. Ya. Popkova、E. I. Mysov、M. V. Galakhov、V. K. Osmanov、L. S. German

  DOI：10.1007/bf01184548

  日期：1990.12

  A new method has been developed for the synthesis of perfluorinated alpha,beta-unsaturated thiocyanates by the reaction of the corresponding sulfenyl chlorides with KCN in water. The thiocyanate form of perfluoro-2-methyl-2-pentene-3-thiocyanate was isomerized to the isothiocyanate form. This rearrangement is initiated by both fluoride and thiocyanate anions.
• Bekker, R. A.; Popkova, V. Ya.; Knunyants, I. L., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya
  作者：Bekker, R. A.、Popkova, V. Ya.、Knunyants, I. L.

  DOI：——

  日期：——
• Functionalization of alkenes by polyfluorinated α,β-unsaturated sulfenyl chlorides: reactions of 2-chloroperfluoro-1-cyclohexenesulfenyl chloride-1 with activated olefins
  作者：V.Ya. Popkova、V.K. Osmanov、A.V. Borisov、A.I. Lutsenko、A.F. Aerov、E.I. Mysov、M.V. Galachov、I.V. Bodrikov

  DOI：10.1016/s0022-1139(00)80852-0

  日期：1993.12

  A variety of beta-chlorothioethers have been obtained by the reaction of 2-chloroperfluoro-1-cyclohexenesulfenyl chloride-1 (I) with t-butylethene, styrene, allylbenzene and p-methoxyallylbenzene in CH2Cl2 or CH3NO2. Skeletal rearrangement with 1,2-migration of the p-methoxyphenyl group occurs on reaction of I with p-methoxyallylbenzene along with the formation of addition products (Markovnikov and anti-Markovnikov adducts). A possible additive salt effect (LiClO4/CH3NO2 system) has been examined for the reaction of I with t-butylethene, allylbenzene and p-methoxyallylbenzene; the effect is noted only in the case of t-butylethene, when intramolecular rearrangement with 1,2-migration of the methyl group takes place.