(2-tert-Butyl-4-methyl-phenoxy)-trimethyl-silane | 134291-10-4

• 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: (2-tert-Butyl-4-methyl-phenoxy)-trimethyl-silane
• 英文别名: 2-tert-Butyl-4-methylphenol, TMS；(2-tert-butyl-4-methylphenoxy)-trimethylsilane
• CAS: 134291-10-4
• 化学式: C₁₄H₂₄OSi
• 分子量: 236.429
• InChiKey: LNNNQHWUBSUOCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  三氯一茂钛 、 (2-tert-Butyl-4-methyl-phenoxy)-trimethyl-silane 以 neat (no solvent) 为溶剂， 生成
  参考文献：
  名称：

  Steric influences in cyclopentadienyl-monophenoxide complexes of titanium(iv) arising from ortho-substitution of the phenoxide ligand

  摘要：

  Reaction of [CpTiCl3] with 1 equiv. of Me3SiOC6H4CMe3-4 in benzene or themalisation with an excess of neat Me3SiOC6H4CMe3-4 gives good yields of crystalline [CpTiCl2(OC6H4CMe3-4)] (1) for which an X-ray crystal structure determination shows a distorted tetrahedral geometry. Reaction of [CpTiCl3] and Me3SiOC6H3CMe3-2-Me-4 via the benzene solvent method or the direct thermalisation gives rise to crystalline [CpTiCl2(OC6H3CMe3-2-Me-4)] (2) for which an X-ray crystal structure determination shows a distorted tetrahedral geometry little changed from complex 1 but with the phenoxide ligand ring rotated so that two of the tert-butyl group methyls straddle one chloro ligand. Refluxing [CpTiCl3] and Me3SiOC6H4Ph-4 in toluene gave crystalline [CpTiCl2(OC6H4Ph-2)] (3) which X-ray crystallography shows has a distorted tetrahedral geometry little changed from 1 or 2. The phenoxide ligand ring is rotated less in I than in 2 or 3 with the 2-phenyl substituent sited between the chloro and Cp ligands. The complexes differ only in the interplanar angle between the Cp and phenoxide ligand phenyl rings [6.4(1)degrees for 1, 29.4(1)degrees for 2 and 22.2(1)degrees for 3]. DFT calculations carried out on 2 are in good agreement with the X-ray crystal structure. A relaxed PES scan shows that the tert-butyl group in the complex cannot freely rotate past the adjacent chloro ligand and is essentially locked in close proximity to it. There is a shallow minimum (2 kJ/mol within a range of 60 degrees) for the Ti-O-C-C dihedral angle indicating there is sufficient torsional motion within the molecule to accommodate the tert-butyl group in the observed position. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.11.016
• 作为产物：
  描述：

  叔-丁基对甲酚 生成 (2-tert-Butyl-4-methyl-phenoxy)-trimethyl-silane
  参考文献：
  名称：

  LAUTERBUCH, MANFRED;JUGER, GUNTER;JANCKE, HARALD;LEHMANN, ANDREAS;ZIMMERM+, CHEM. TECHN. , 42,(1990) N, C. 264-268

  摘要：

  DOI：

文献信息

• Protection of hydroxy groups as trimethylsilyl ethers using 1,1,1,3,3,3-hexamethyldisilazane (HMDS) catalyzed by poly(4-vinylpyridinium tribromide)
  作者：Arash Ghorbani-Choghamarani、Mohammad Ali Zolfigol、Maryam Hajjami、Khorshid Darvishi、Laleh Gholamnia

  DOI：10.1135/cccc2009560

  日期：——

  A very efficient procedure for the protection of alcohols and phenols is presented. The mixture of 1,1,1,3,3,3-hexamethyldisilazane (HMDS) and catalytic amounts of poly(4-vinylpyridinium tribromide) was found to be effective for the trimethylsilylation of alcohols and phenols. Protection reaction is very simple and performs heterogeneously in acetonitrile at room temperature under mild conditions.

  一种非常高效的醇和酚保护程序被提出。发现1,1,1,3,3,3-六甲基二硅氮烷（HMDS）与聚（4-乙烯吡啶三溴化物）的催化量混合物对醇和酚的三甲基硅基化是有效的。保护反应非常简单，在室温下在乙腈中以温和条件异相进行。
• Application of a novel nano-immobilization of ionic liquid on an MCM-41 system for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
  作者：Mohammad Ali Zolfigol、Sami Sajjadifar、Arash Ghorbani-Choghamarani、Farzaneh Tami

  DOI：10.1007/s11164-018-3544-4

  日期：2018.11

  3-[(3-(Trisilyloxy)propyl)chloride]-1-methylimidazolium tribromide ionic liquid supported on MCM-41 [nano-MCM-41@(CH2)3-1-methylimidazole]Br3 as a novel heterogeneous nano-catalyst was easily prepared and characterized using FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, thermogravimetric analysis, differential thermal analysis, and differential thermogravimetric analysis. This

  负载在MCM-41 [nano-MCM-41 @（CH 2）3 -1-甲基咪唑] Br 3上的3-[（3-（三甲硅烷基氧基）丙基）氯化物] -1-甲基咪唑鎓离子液体FT-IR光谱，扫描电子显微镜，X射线衍射，热重分析，差示热分析和差示热重分析很容易制备和表征新型多相纳米催化剂。在室温下，使用六甲基二硅氮烷在二氯甲烷中，该催化剂成功地用于各种醇（伯醇，仲醇和叔醇）以及各种酚的选择性三甲基甲硅烷基化反应生成相应的三甲基甲硅烷基（TMS）醚。该方法具有许多优点，例如反应时间短，产物的收率高至优异，并且易于回收和再利用催化剂。
• Heterogeneous Catalysis in Trimethylsilylation of Alcohols and Phenols by Zirconium Sulfophenyl Phosphonate
  作者：Massimo Curini、Francesco Epifano、Maria Carla Marcotullio、Ornelio Rosati、Umberto Costantino

  DOI：10.1080/00397919908085797

  日期：1999.2

  Layered zirconium sulfophenyl phosphonate was found to be an efficient heterogeneous catalyst for the trimethylsilylation of alcohols and phenols.