trimethyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-iodododecyl)silane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trimethyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-iodododecyl)silane
• 英文别名: Trimethyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-iodododecyl)silane；(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-iodododecyl)-trimethylsilane
• 化学式: C₁₅H₁₂F₂₁ISi
• 分子量: 746.217
• InChiKey: GJKIQJYPVLFGDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.34
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  trimethyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-iodododecyl)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以97.1%的产率得到1H,1H,2H-全氟-1-十二烯
  参考文献：
  名称：

  Application of Trimethylvinylsilane as a Convenient Synthetic Precursor of (Perfluoroalkyl)ethenes:  An Unusual Fluoride-Induced Elimination−Desilylation Coupled Reaction

  摘要：

  [GRAPHICS]A convenient and effective method for the preparation of perfluoroalkylated ethenes is described. First, the free radical addition of perfluoroalkyl iodides to trimethylvinylsllane in the presence of AlBN gave iodoethylsilane intermediates (F(CF(2))(n)CH(2)CHISiMe(3), n = 4 (1), 6 (2), 8 (3), 10 (4); 94-99%). Then an unusual dehydrohalogenation-desilylation reaction was effected by tetrabutylammonium fluoride, and finally the product isolation (F(CF(2))(n)CH=CH(2) (5-8), 62-87%) was facilitated using a fluorous phase separation technique. This novel approach can also be applied to adjust short C(2) hydrocarbon units to functionalized fluorinated segments (e.g., HOCH(2)(CF(2))(8)CH=CH(2) (11), 71%), All structures were verified by state-of-the-art multinuclear one- and two-dimensional NMR experiments involving both homo- ((19)F-(19)F) and heteronuclear ((1)H-(13)C, (19)F-(13)C) correlations based on the GMQFCOPS and inverse (1)H and/or (19)F detected GHSQC, GHMQC sequences with broad-band adiabatic (13)C decoupling.

  DOI：

  10.1021/ol006105o
• 作为产物：
  描述：

  1-碘全氟癸烷 、 乙烯基三甲基硅烷 以 neat (no solvent) 为溶剂， 反应 7.0h， 以46%的产率得到trimethyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-iodododecyl)silane
  参考文献：
  名称：

  乙烯基硅烷的高选择性光诱导全氟烷基化及其在合成水基聚硅烷中的应用

  摘要：

  聚硅烷的官能化是材料科学中的重要课题，因为预计官能化的聚硅烷会表现出潜在的创新性能。这项研究的目的是通过将全氟烷基引入骨架来增加聚硅烷的除水性能。在氙气灯照射下，各种乙烯基硅烷的光诱导碘全氟烷基化成功进行：乙烯基单硅烷与全氟烷基碘进行碘全氟烷基化（R fI）区域选择性地，以中等至高产率获得相应的全氟烷基化硅烷。已经研究了光诱导的碘全氟烷基化的详细优化，以将该方法应用于聚硅烷的官能化。具有乙烯基的聚硅烷可以通过在可见光照射下二氯乙烯基硅烷与二碘化sa（SmI 2）和）金属（Sm）的还原偶联来合成。依次将合成的乙烯基聚硅烷和R f I（约1.0 mM CHCl 3溶液）涂覆在玻璃板上，然后随后用波长超过300 nm的光进行光辐照，成功地为玻璃板增加了出色的滤水性能。

  DOI：

  10.1007/s11164-016-2424-z

文献信息

• Application of Trimethylvinylsilane as a Convenient Synthetic Precursor of (Perfluoroalkyl)ethenes:  An Unusual Fluoride-Induced Elimination−Desilylation Coupled Reaction
  作者：Zoltán Szlávik、Gábor Tárkányi、Ágnes Gömöry、József Rábai

  DOI：10.1021/ol006105o

  日期：2000.7.1

  [GRAPHICS]A convenient and effective method for the preparation of perfluoroalkylated ethenes is described. First, the free radical addition of perfluoroalkyl iodides to trimethylvinylsllane in the presence of AlBN gave iodoethylsilane intermediates (F(CF(2))(n)CH(2)CHISiMe(3), n = 4 (1), 6 (2), 8 (3), 10 (4); 94-99%). Then an unusual dehydrohalogenation-desilylation reaction was effected by tetrabutylammonium fluoride, and finally the product isolation (F(CF(2))(n)CH=CH(2) (5-8), 62-87%) was facilitated using a fluorous phase separation technique. This novel approach can also be applied to adjust short C(2) hydrocarbon units to functionalized fluorinated segments (e.g., HOCH(2)(CF(2))(8)CH=CH(2) (11), 71%), All structures were verified by state-of-the-art multinuclear one- and two-dimensional NMR experiments involving both homo- ((19)F-(19)F) and heteronuclear ((1)H-(13)C, (19)F-(13)C) correlations based on the GMQFCOPS and inverse (1)H and/or (19)F detected GHSQC, GHMQC sequences with broad-band adiabatic (13)C decoupling.
• Highly selective photoinduced perfluoroalkylation of vinylsilanes and its application to synthesis of water-shedding polysilanes
  作者：Aya Yoshimura、Akihiro Nomoto、Mari Uchida、Hiroki Kusano、Tomokazu Saeki、Akiya Ogawa

  DOI：10.1007/s11164-016-2424-z

  日期：2017.6

  into their skeleton. The photoinduced iodoperfluoroalkylation of various vinylsilanes takes place successfully upon irradiation with a xenon lamp: vinylmonosilanes undergo iodoperfluoroalkylation with perfluoroalkyl iodides (RfI) regioselectively, and the corresponding perfluoroalkylated silanes are obtained in moderate to high yields. Detailed optimization of the photoinduced iodoperfluoroalkylation

  聚硅烷的官能化是材料科学中的重要课题，因为预计官能化的聚硅烷会表现出潜在的创新性能。这项研究的目的是通过将全氟烷基引入骨架来增加聚硅烷的除水性能。在氙气灯照射下，各种乙烯基硅烷的光诱导碘全氟烷基化成功进行：乙烯基单硅烷与全氟烷基碘进行碘全氟烷基化（R fI）区域选择性地，以中等至高产率获得相应的全氟烷基化硅烷。已经研究了光诱导的碘全氟烷基化的详细优化，以将该方法应用于聚硅烷的官能化。具有乙烯基的聚硅烷可以通过在可见光照射下二氯乙烯基硅烷与二碘化sa（SmI 2）和）金属（Sm）的还原偶联来合成。依次将合成的乙烯基聚硅烷和R f I（约1.0 mM CHCl 3溶液）涂覆在玻璃板上，然后随后用波长超过300 nm的光进行光辐照，成功地为玻璃板增加了出色的滤水性能。