4-(perfluorohexylsulfanyl)-phenol | 551935-36-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(perfluorohexylsulfanyl)-phenol
• 英文别名: 4-((perfluorohexyl)thio)phenol；4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexylsulfanyl)phenol
• CAS: 551935-36-5
• 化学式: C₁₂H₅F₁₃OS
• 分子量: 444.216
• InChiKey: XLOGTWCSNOUIEF-UHFFFAOYSA-N

物化性质

• 熔点：
  28-30 °C
• 沸点：
  253.1±40.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(perfluorohexylsulfanyl)-phenol 在 甲烷磺酸 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、4.5 kPa 条件下， 反应 30.0h， 生成 (4-perfluorohexylsulfanyl-phenyl)-(R)-4,6-O-[4'-(4-perfluorohexylsulfanyl)-benzoyloxy]-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents

  摘要：

  The perfluorohexyl-aryl-thioethers 3 and 4, building blocks for the synthesis of the chiral target mesogens 12-15, were prepared by dithionite-mediated S-perfluoroalkylation of the p-substituted thiophenols 1 and 2. The phenolic HO- group of 3 was O-glucosylated with pentaacetyl-D-glucopyranose to 5 followed by deacetylation forming the tetrol 6 and by acetalizing with 4-(4-perfluorohexylsulfanylbenzoyloxy)-benzaldehyde-dimethylacetal (8) generating the dihydroxy-intermediate 9. The latter contains two perfluorohexylthio chains. Alternatively, the dimethylacetal 8 was linked to p-octylphenyl-beta-(D)-glucopyranoside (10) giving the mixed octyl/perfluorohexyl substituted p-octylphenyl-4,6-O-[4'-(4"-perfluorohexylsulfanyl)-benzoyloxy]-benzylidene-beta-(D)-glucopyranoside (11). Compound 8 was obtained via esterification of 4 with p-hydroxy-benzaldehyde to 4-(4-perfluorohexylsulfanyl-benzoyloxy)-benzaldehyde (7). Finally, the diols 9 and 11 were dehydroxylated to 12 and 13 followed by hydrogenation yielding 14 and 15, respectively. Tetrol 6, diols 9, 11 and the non-amphiphilic compounds 7, 12-15 are thermotropic liquid crystals. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00310-x
• 作为产物：
  描述：

  4-羟基苯硫酚 、 sodium perfluorohexylsulfinate 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以67%的产率得到4-(perfluorohexylsulfanyl)-phenol
  参考文献：
  名称：

  Silver-catalyzed fluoroalkylation of thiols using fluoroalkanesulfinates

  摘要：

  A practical sliver-catalyzed fluoroalkylation of aryl-, heteroaryl- and allcylthiols has been developed. The reaction has a good functional-group tolerance and excellent selectivity. A variety of stable and solid fluoroalkanesulfinates including di- and perfluoroalkanesulfinates can be employed. This methodology provides a straightforward and streamlined access to perfluoroallcylthiolated organic molecules.[GRAPHICS](C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2016.11.010