bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide | 96497-21-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide
• 英文别名: Bis[2-(heptadecafluorooctyl)ethyl] sulfide；1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)decane
• CAS: 96497-21-1
• 化学式: C₂₀H₈F₃₄S
• 分子量: 926.295
• InChiKey: HINXQBCQQBVCIK-UHFFFAOYSA-N

物化性质

• 沸点：
  349.4±42.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide 在 过氧乙酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 0.25h， 以85%的产率得到bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfoxide
  参考文献：
  名称：

  Syntheses, oxidations, and palladium complexes of fluorous dialkyl sulfides: new precursors to highly active catalysts for the Suzuki coupling

  摘要：

  Reactions of Rf(8)(CH2)(n)I(R-f8=CF3(CF2)(7)) with Li2S give the fluorous dialkyl sulfides (R-f8(CH2)(n))(2)S (n=2, 1, 71%; 3, 2, 67%) as low melting white solids that are soluble in most fluorous and organic solvents. Reactions of 1 and 2 with CH3CO3H yield the corresponding sulfoxides (R-f8(CH2)(n))(2)S=O (85; 80%), which are soluble in CF3C6F5 at room temperature, but insoluble in most other solvents. At higher temperatures, solubilities can become appreciable. Reactions of 1 and 2 with Na2PdCl4 (ca. 0.5 equiv.) give palladium complexes [(R-f8(CH2)(n))(2)S](2)PdCl2 (5, 94%; 6, 95%), which are soluble in only a limited range of fluorinated solvents at room temperature. The CF3C6F11/toluene partition coefficients of 1 and 2 are 98.7:1.3 and 96.6:3.4 (24degreesC). The Suzuki coupling of aryl bromides and PhB(OH)(2) to biaryls is catalyzed by 5 and 6 (0.02 mol%) in CF3C6F11/DMF/H2O in the presence of K3PO4, generally at room temperature. Turnover numbers of 4500-5000 are easily achieved. However, activities decrease under fluorous biphase recycling conditions, and implications for the nature of the catalytically active species are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00275-2
• 作为产物：
  描述：

  1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-十七氟-10-碘庚烷 在 三乙基硼氢化锂 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide
  参考文献：
  名称：

  Syntheses, oxidations, and palladium complexes of fluorous dialkyl sulfides: new precursors to highly active catalysts for the Suzuki coupling

  摘要：

  Reactions of Rf(8)(CH2)(n)I(R-f8=CF3(CF2)(7)) with Li2S give the fluorous dialkyl sulfides (R-f8(CH2)(n))(2)S (n=2, 1, 71%; 3, 2, 67%) as low melting white solids that are soluble in most fluorous and organic solvents. Reactions of 1 and 2 with CH3CO3H yield the corresponding sulfoxides (R-f8(CH2)(n))(2)S=O (85; 80%), which are soluble in CF3C6F5 at room temperature, but insoluble in most other solvents. At higher temperatures, solubilities can become appreciable. Reactions of 1 and 2 with Na2PdCl4 (ca. 0.5 equiv.) give palladium complexes [(R-f8(CH2)(n))(2)S](2)PdCl2 (5, 94%; 6, 95%), which are soluble in only a limited range of fluorinated solvents at room temperature. The CF3C6F11/toluene partition coefficients of 1 and 2 are 98.7:1.3 and 96.6:3.4 (24degreesC). The Suzuki coupling of aryl bromides and PhB(OH)(2) to biaryls is catalyzed by 5 and 6 (0.02 mol%) in CF3C6F11/DMF/H2O in the presence of K3PO4, generally at room temperature. Turnover numbers of 4500-5000 are easily achieved. However, activities decrease under fluorous biphase recycling conditions, and implications for the nature of the catalytically active species are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00275-2

文献信息

• Synthesis of terminally perfluorinated long-chain alkanethiols, sulfides and disulfides from the corresponding halides
  作者：C Naud、P Calas、H Blancou、A Commeyras

  DOI：10.1016/s0022-1139(00)00215-3

  日期：2000.7

  prepared by various synthetic methods, starting from the corresponding iodides or bromides. Methods based on sodium hydrogen sulfide, commonly used to accomplish this conversion, treatment of the Bunte salt obtained from sodium thiosulfate, the basic hydrolysis of isothiouronium salts, the hydrolysis under mild conditions of thiophosphorates formed from sodium thiophosphate and the basic hydrolysis of thiol

  半氟化Ñ -alkanethiols，对称硫化物和二硫化物轴承链（一个或多个）F（CF 2）Ñ（CH 2）米与Ñ = 4，6，8，10，和米从相应的碘化物或溴化物开始，＝ 2、11已经通过各种合成方法制备。通常基于硫化氢钠的方法来完成这种转化，处理从硫代硫酸钠制得的邦特盐，异硫脲鎓盐的碱性水解，在温和条件下由硫代磷酸钠形成的硫代磷酸酯的水解以及硫醇乙酸的碱性水解相对于标题化合物的选择性合成，已研究并比较了其衍生物。硫代乙酸路线基本上产生带有一些二硫化物的硫醇。硫脲的结果似乎相似。硫代磷酸钠是合成硫醚的极佳途径，尤其是从溴化物开始时。基于硫化氢钠和硫代硫酸钠的两种经典方法显示出较差的选择性。有可能获得纯净状态下报告的所有硫化合物。
• US6391948B1
  申请人：——

  公开号：US6391948B1

  公开（公告）日：2002-05-21
• [EN] TRIAZINE COMPOUNDS AND USE AS WATER REPELLENT<br/>[FR] COMPOSES DE TRIAZINE ET LEUR UTILISATION EN TANT QU'AGENT HYDROFUGE
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2001044209A1

  公开（公告）日：2001-06-21

  The invention describes fluorochemical triazine compounds, compositions containing the fluorochemical triazine compounds, the process for preparing the fluorochemical compounds and compositions, substrates treated with the fluorochemical compounds, melt extrusion of fibers and films containing the fluorochemical compounds and compositions, and coating, polish and marine antifouling compositions to provide oil and water repellency to substrates.
• Syntheses, oxidations, and palladium complexes of fluorous dialkyl sulfides: new precursors to highly active catalysts for the Suzuki coupling
  作者：Christian Rocaboy、J.A Gladysz

  DOI：10.1016/s0040-4020(02)00275-2

  日期：2002.5

  Reactions of Rf(8)(CH2)(n)I(R-f8=CF3(CF2)(7)) with Li2S give the fluorous dialkyl sulfides (R-f8(CH2)(n))(2)S (n=2, 1, 71%; 3, 2, 67%) as low melting white solids that are soluble in most fluorous and organic solvents. Reactions of 1 and 2 with CH3CO3H yield the corresponding sulfoxides (R-f8(CH2)(n))(2)S=O (85; 80%), which are soluble in CF3C6F5 at room temperature, but insoluble in most other solvents. At higher temperatures, solubilities can become appreciable. Reactions of 1 and 2 with Na2PdCl4 (ca. 0.5 equiv.) give palladium complexes [(R-f8(CH2)(n))(2)S](2)PdCl2 (5, 94%; 6, 95%), which are soluble in only a limited range of fluorinated solvents at room temperature. The CF3C6F11/toluene partition coefficients of 1 and 2 are 98.7:1.3 and 96.6:3.4 (24degreesC). The Suzuki coupling of aryl bromides and PhB(OH)(2) to biaryls is catalyzed by 5 and 6 (0.02 mol%) in CF3C6F11/DMF/H2O in the presence of K3PO4, generally at room temperature. Turnover numbers of 4500-5000 are easily achieved. However, activities decrease under fluorous biphase recycling conditions, and implications for the nature of the catalytically active species are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.