trimethyl(4-fluorophenoxy)silane | 18840-04-5

• 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: trimethyl(4-fluorophenoxy)silane
• 英文别名: 4-Fluorphenoxy-trimethylsilan；p-Fluorphenyl-trimethylsilyloxid；(4-fluorophenoxy)trimethyl-silane；(4-Fluoro-phenoxy)-trimethyl-silane；(4-fluorophenoxy)-trimethylsilane
• CAS: 18840-04-5
• 化学式: C₉H₁₃FOSi
• 分子量: 184.286
• InChiKey: DWVUOPAHSBQWNR-UHFFFAOYSA-N

物化性质

• 沸点：
  177-178 °C
• 密度：
  1.0184 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trimethyl(4-fluorophenoxy)silane 在 甲醇 、 1,3-disulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.07h， 以99%的产率得到4-氟苯酚
  参考文献：
  名称：

  Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes

  摘要：

  Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR. H-1 NMR, C-13 NMR and MS studies. All the products were extensively characterized by IR, H-1 NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.08.002
• 作为产物：
  描述：

  4-氟苯酚 、 六甲基二硅氮烷 在 saccharin sodium salt 作用下， 反应 2.0h， 以90%的产率得到trimethyl(4-fluorophenoxy)silane
  参考文献：
  名称：

  六氟苯与三甲基甲硅烷基醚的反应

  摘要：

  六氟苯容易与各种三甲基甲硅烷基醚ROSiMe 3（R = CF 3 CH 2，FCH 2 CH 2，H（CF 2）n，CH 2（n = 2，4），CF 3（CF 2）6 CH 2，CF 3（CF 2）5 CH 2 CH 2，Me 3 SiOCH 2 CH 2，C 6 F 5 OCH 2 CH 2，C 6ħ 5，4-FC 6 H ^ 4），以从单环至hexapolyfluoroalkoxy-和polyfluoroaryloxy基苯得到。通过单晶X射线分析确认了C 6（OCH 2 CF 3）6的结构。全氟化醚C 6 F 5 OCF 2 CF 3可以通过氯化和随后用SbF 3 / SbCl 5氟化由C 6 F 5 OCH 2 CF 3合成。还讨论了5,6,7,8-四氟-1,4-苯并二恶烷的氯化反应。

  DOI：

  10.1016/0022-1139(93)05008-o

文献信息

• Preparation of Silica Supported Tin Chloride: As a Recyclable Catalyst for the Silylation of Hydroxyl Groups with HMDS
  作者：Khodabakhsh Niknam、Mohammad Ali Zolfigol、Dariush Saberi、Hajar Molaee

  DOI：10.1002/jccs.200900181

  日期：2009.12

  Silica‐supported tin chloride [SiO2‐Sn(Cl)4‐n] has been prepared by mixing tin chloride with activated silica gel in toluene under refluxing conditions for one day. A range of primary, secondary, and tertiary alcohols as well as phenolic hydroxyl groups were converted into their corresponding trimethylsilyl ethers with hexamethyldisilazane in the presence of catalytic amounts of silica‐supported tin

  硅胶负载的氯化锡[SiO 2 -Sn（Cl）4-n ]是通过在回流条件下将氯化锡和活性硅胶在甲苯中混合一天来制备的。在室温下，在催化量的二氧化硅负载的氯化锡存在下，一系列的伯，仲和叔醇以及酚羟基被六甲基二硅氮烷转化为相应的三甲基甲硅烷基醚。还观察到在其他官能团存在下羟基的优异的化学选择性甲硅烷基化。该催化剂可以循环使用十五次而不会损失效率。
• Silica-bonded<i>S</i>-sulfonic acid as a recyclable catalyst for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS)
  作者：Khodabakhsh Niknam、Dariush Saberi、Hajar Molaee、Mohammad Ali Zolfigol

  DOI：10.1139/v09-162

  日期：2010.2

  Silica-bonded S-sulfonic acid (SBSSA) was prepared by the reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in tert-butylmethyl ether, and used as a catalyst for the silylation of hy...

  由3-巯基丙基二氧化硅（MPS）与氯磺酸在叔丁基甲基醚中反应制备二氧化硅键合S-磺酸（SBSSA），用作甲硅烷基化的催化剂。
• Alkyl Aryl Ether Bond Formation with PhenoFluor
  作者：Xiao Shen、Constanze N. Neumann、Claudia Kleinlein、Nathaniel W. Goldberg、Tobias Ritter

  DOI：10.1002/anie.201500902

  日期：2015.5.4

  An alkyl aryl ether bond formation reaction between phenols and primary and secondary alcohols with PhenoFluor has been developed. The reaction features a broad substrate scope and tolerates many functional groups, and substrates that are challenging for more conventional ether bond forming processes may be coupled. A preliminary mechanistic study indicates reactivity distinct from conventional ether

  已经开发出苯酚与伯醇和仲醇与 PhenoFluor 之间的烷基芳基醚键形成反应。该反应具有广泛的底物范围和耐受许多官能团的特点，并且可以偶联对更传统的醚键形成过程具有挑战性的底物。初步的机理研究表明其反应性不同于传统的醚键形成。
• Synthesis of (η6-arene)(η5-cyclopentadienyl) iron (II) complexes with heteroatom and carbonyl substituents. Part I: Oxygen and carbonyl substituents
  作者：R.M.G. Roberts

  DOI：10.1016/j.jorganchem.2005.12.070

  日期：2006.6

  used to introduce oxygen substituents into (η-arene)(η-cyclopentadienyl) iron (II) complexes. Photochemical ligand exchange led to the formation of the first recorded trioxygenated complex as well as mono- and di-oxygenated species. Using microwave techniques, reaction times for SNAr displacement reactions of halobenzene complexes by phenols were reduced from several hours to a few minutes. Phenols protected

  已使用一系列反应将氧取代基引入（η-芳烃）（η-环戊二烯基）铁（II）络合物中。光化学配体交换导致形成第一个记录的三加氧配合物以及单加氧和双加氧物质。使用微波技术，通过苯酚进行卤代苯配合物的S N Ar置换反应的反应时间从数小时减少至数分钟。苯酚受任一t保护使用常规的热配体交换反应，发现-丁基化或三甲基甲硅烷基化产生适量的相应酚配合物。没有这种保护，收率极低。上述方法导致二羟基苯配合物的第一实例的合成。还报告了一些其他合成方法。
• Selective hydrogenation of fluorinated arenes using rhodium nanoparticles on molecularly modified silica
  作者：Souha Kacem、Meike Emondts、Alexis Bordet、Walter Leitner

  DOI：10.1039/d0cy01716g

  日期：——

  arenes using Rh nanoparticles on molecularly modified silica supports (Rh@Si–R) as highly effective and recyclable catalysts. The catalyst preparation comprises grafting non-polar molecular entities on the SiO2 surface generating a hydrophobic environment for controlled deposition of well-defined rhodium particles from a simple organometallic precursor. A broad range of fluorinated cyclohexane derivatives

  氟化环己烷衍生物的生产是通过在分子改性的二氧化硅载体（Rh @ Si–R）上作为高效且可回收的催化剂，使用Rh纳米粒子对易得的氟化芳烃进行选择性氢化来完成的。催化剂制备包括将非极性分子实体接枝在SiO 2表面上，从而产生疏水性环境，以控制从简单的有机金属前体中沉淀出明确的铑颗粒。各种氟化环己烷衍生物被证明具有出色的功效（0.05–0.5 mol％Rh，10–55 bar H 2，80–100°C，1-2小时），包括与工业相关的构建基块。添加CaO作为痕量HF的清除剂可大大提高催化体系的可回收性，并防止与HF存在相关的风险，而不会影响反应的活性和选择性。