4-tridecafluorohexylstyrene | 159241-93-7

• 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: 4-tridecafluorohexylstyrene
• 英文别名: 1-(perfluorohexyl)-4-vinylbenzene；1-(Perfluorohexyl)-4-vinylbenzene；1-ethenyl-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)benzene
• CAS: 159241-93-7
• 化学式: C₁₄H₇F₁₃
• 分子量: 422.189
• InChiKey: ZAPLIHGXGRXHJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 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：
  0.43
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-tridecafluorohexylstyrene 在 dihydrogen hexachloroplatinate 三氯硅烷 作用下， 以 甲醇 为溶剂， 生成 Trichloro-[1-(4-tridecafluorohexyl-phenyl)-ethyl]-silane 、 Trichloro-[2-(4-tridecafluorohexyl-phenyl)-ethyl]-silane
  参考文献：
  名称：

  Synthesis of a silane coupling agent containing a 4-(perfluoroalkyl)phenyl group and its application to the surface modification of glass

  摘要：

  Eight silane coupling agents, CF3(C6H4)C2H4Si(CH3)(OCH3)(2) (C6H4=p-phenylene) (1), C4F9(C6H4)C2H4Si(CH3)(OCH3)(2) (2), C6F13(C6H4)C2H4Si(CH3)(OCH3)(2) (3), C8F17(C6H4)C2H4Si(CH3)(OCH3)(2) (4), CF3(C6H4)C2H4Si(OCH3)(3) (5), C4F9(C4H4)C2H4Si-(OCH3)(3) (6), C6F13(C6H4)C2H4Si(OCH3)(3) (7) and C8F17(C6H4)C2H4Si(OCH3)(3) (8) have been prepared by the hydrosilylation reaction of dichloro(methyl)silane or trichlorosilane with the corresponding 4-perfluoroalkylstyrene in the presence of hydrogen hexachloroplatinate(IV), followed by reaction with sodium methoxide. These new coupling agents were freely soluble in hydrocarbon solvents. Their application for the surface modification of glass has been attempted. From measurements of the contact angles theta (degrees) of water and oleic acid on a modified glass plate surface, it was found that the silane coupling agents show a high degree of surface modification. The oxidation resistance of the modified glass surface has also been investigated.

  DOI：

  10.1016/0022-1139(94)03165-v
• 作为产物：
  描述：

  1-(4'-tridecafluorohexylphenyl)ethanol 在 potassium hydrogensulfate 作用下， 以 甲苯 为溶剂， 以89.4%的产率得到4-tridecafluorohexylstyrene
  参考文献：
  名称：

  Synthesis of a silane coupling agent containing a 4-(perfluoroalkyl)phenyl group and its application to the surface modification of glass

  摘要：

  Eight silane coupling agents, CF3(C6H4)C2H4Si(CH3)(OCH3)(2) (C6H4=p-phenylene) (1), C4F9(C6H4)C2H4Si(CH3)(OCH3)(2) (2), C6F13(C6H4)C2H4Si(CH3)(OCH3)(2) (3), C8F17(C6H4)C2H4Si(CH3)(OCH3)(2) (4), CF3(C6H4)C2H4Si(OCH3)(3) (5), C4F9(C4H4)C2H4Si-(OCH3)(3) (6), C6F13(C6H4)C2H4Si(OCH3)(3) (7) and C8F17(C6H4)C2H4Si(OCH3)(3) (8) have been prepared by the hydrosilylation reaction of dichloro(methyl)silane or trichlorosilane with the corresponding 4-perfluoroalkylstyrene in the presence of hydrogen hexachloroplatinate(IV), followed by reaction with sodium methoxide. These new coupling agents were freely soluble in hydrocarbon solvents. Their application for the surface modification of glass has been attempted. From measurements of the contact angles theta (degrees) of water and oleic acid on a modified glass plate surface, it was found that the silane coupling agents show a high degree of surface modification. The oxidation resistance of the modified glass surface has also been investigated.

  DOI：

  10.1016/0022-1139(94)03165-v

文献信息

• Synthesis of a Polymerizable Fluorosurfactant for the Construction of Stable Nanostructured Proton-Conducting Membranes
  作者：Mohan N. Wadekar、Wolter F. Jager、Ernst J. R. Sudhölter、Stephen J. Picken

  DOI：10.1021/jo101196w

  日期：2010.10.15

  related fluorocarbon compounds is described. Compound 1 is synthesized using a copper-mediated cross-coupling reaction of 4-bromobenzaldehyde and sodium 5-iodooctafluoro-3-oxapentanesulfonate. The resulting benzaldehyde is converted to a styrene unit using a Wittig reaction with methyltriphenylphosphonium bromide in acetonitrile, using DBU as a base. This strategy for converting an iodo-functionalized

  可聚合氟化表面活性剂1,1,2,2-四氟-2-（1,1,2,2-四氟-2-（4-乙烯基苯基）乙氧基）乙磺酸钠（1）和许多相关碳氟化合物的合成描述了化合物。化合物1使用4-溴苯甲醛和5-碘八氟-3-氧杂戊磺酸磺酸钠的铜介导的交叉偶联反应合成了α-己内酰胺。使用DBU作为碱，通过与甲基三苯基溴化in在乙腈中的维蒂希反应，将生成的苯甲醛转化为苯乙烯单元。这种将碘官能化的含氟表面活性剂转化为含苯乙烯的含氟表面活性剂的策略是高效的，因为两个反应均在极性溶剂中进行并且与磺酸盐部分相容。此外，铜可介导的交叉偶联反应对于电子贫乏的芳基溴化物（如4-溴苯甲醛）最为有效。我们希望采用1通过1的聚合反应来构建纳米结构膜 在微乳液或溶致液晶相中。
• Copper‐Catalyzed Radical Enantioselective Carbo‐Esterification of Styrenes Enabled by a Perfluoroalkylated‐PyBox Ligand
  作者：Zaicheng Nie、Mong‐Feng Chiou、Jinfeng Cui、Yanjie Qu、Xiaotao Zhu、Wujun Jian、Haigen Xiong、Yajun Li、Hongli Bao

  DOI：10.1002/anie.202202077

  日期：2022.7.11

  The radical enantioselective carbo-esterification of styrenes enabled by a newly developed perfluoroalkylated-PyBox ligand and copper catalysis is reported. Mechanistic studies reveal that this reaction is a rare example of an efficient ligand-decelerated system, in which the ligand decelerates the reaction, but the reaction is still efficient with reduced amounts of ligand.

  报道了通过新开发的全氟烷基化-PyBox 配体和铜催化实现苯乙烯的自由基对映选择性碳酯化。机理研究表明，该反应是有效配体减速系统的罕见例子，其中配体使反应减速，但在配体量减少的情况下反应仍然有效。