1-methyl-3,5-bis-trimethylsilanyloxy-benzene | 89267-67-4

• 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: 1-methyl-3,5-bis-trimethylsilanyloxy-benzene
• 英文别名: Benzene, 1-methyl-3,5-bis[(trimethylsilyl)oxy]-；trimethyl-(3-methyl-5-trimethylsilyloxyphenoxy)silane
• CAS: 89267-67-4
• 化学式: C₁₃H₂₄O₂Si₂
• 分子量: 268.503
• InChiKey: ILCZPWVHDICNLU-UHFFFAOYSA-N

物化性质

• 沸点：
  272.8±28.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)
• 保留指数：
  1446

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-3,5-bis-trimethylsilanyloxy-benzene 在 甲醇 、 1,3-disulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.1h， 以99%的产率得到3,5-二羟基甲苯
  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：

  3,5-二羟基甲苯 生成 1-methyl-3,5-bis-trimethylsilanyloxy-benzene
  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

• Polyhalogenated heterocyclic compounds
  作者：Richard D. Chambers、Ali Khalil、Christopher B. Murray、Graham Sandford、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/j.jfluchem.2005.01.018

  日期：2005.7

  Model studies show that displacement of fluorine, rather than chlorine, occurs upon reaction of 3,5-dichloro-2,4,6-trifluoropyridine with sodium methoxide and phenoxide. Subsequent hydro-dechlorination can be achieved by reaction with lithium aluminium hydride whereas reaction of sodium in iso-propanol leads to formation of the tri-iso-propoxy pyridine derivative, via nucleophilic substitution of the

  模型研究表明，当3,5-二氯-2,4,6-三氟吡啶与甲醇钠和酚盐反应时，会发生氟而不是氯的置换。随后的加氢脱氯化氢可通过与氢化铝锂反应来实现，而钠在异丙醇中的反应则是通过甲氧基的亲核取代而不是脱氯产物形成三异丙氧基吡啶衍生物。大环化合物可以通过适当的双官能氧亲核试剂与3,5-二氯-2,4,6-三氟吡啶的反应合成，其中一种通过X射线晶体学表征。
• Multicyclic Poly(ether sulfone)s of Phloroglucinol Forming Branched and Cross-Linked Architectures
  作者：Hans R. Kricheldorf、Detlev Fritsch、Lali Vakhtangishvili、Gert Schwarz

  DOI：10.1021/ma021569i

  日期：2003.6.1

  of linear oligomers due to numerous side reactions. In contrast, polycondensations of silylated phloroglucinol under similar conditions were not plagued by such side reactions but involved various cyclization reactions with high efficiency. The MALDI−TOF mass spectra revealed the formation of various cyclic, bicyclic, and multicyclic species of complex structure up to 12 000 Da. Therefore, cross-linking

  钾2 CO 3DMSO中的间苯三酚和4,4'-二氟二苯砜（DFDPS）促进的缩聚反应会由于许多副反应而生成线性低聚物的混合物。相反，在类似条件下甲硅烷基间苯三酚的缩聚反应不会受到此类副反应的困扰，但会涉及各种高效的环化反应。MALDI-TOF质谱揭示了高达12 000 Da的各种复杂结构的环状，双环和多环物种的形成。因此，仅当添加大量过量（+ 30mol％）的DFDPS时才发生交联。所得的支链和交联聚合物主要由环状结构单元组成。由于环化程度高，试图通过将侧基OH基团与磺内酯烷基化引入磺酸基团仅产生了中等程度的取代。
• Polyhalogenated heterocyclic compounds. Macrocycles from perfluoro-4-isopropylpyridinePart 50. For part 49 see ref. 1.
  作者：Richard D. Chambers、Philip R. Hoskin、Alan R. Kenwright、Ali Khalil、Paul Richmond、Graham Sandford、Dmitrii S. Yufit、Judith A. K. Howard

  DOI：10.1039/b303443g

  日期：——

  Perfluoro-4-isopropylpyridine was used as a building block for the two-step synthesis of a variety of macrocyclic systems bearing pyridine sub-units which were characterised by X-ray crystallography. Electrospray mass spectrometry revealed that complexation of either cations and, unusually, anions is possible depending on the structure of the macrocycle.

  全氟-4-异丙基吡啶被用作两步合成多种含吡啶亚基的大环体系的构建模块，这些大环体系通过X射线晶体学进行了表征。电喷雾质谱分析表明，根据大环的结构，阳离子和阴离子（罕见）都有可能发生络合反应。
• Polyhalogenoheterocyclic compounds
  作者：Richard D Chambers、Ali Khalil、Paul Richmond、Graham Sandford、Dmitrii S Yufit、Judith A.K Howard

  DOI：10.1016/j.jfluchem.2003.12.007

  日期：2004.5

  4-Alkoxy-tetrafluoropyridine derivatives were used as building blocks for the synthesis of 14- and 16-membered macrocyclic ring systems comprising pyridine and either poly-ether or amine subunits; two of the macrocycles were characterised by X-ray crystallography.

  4-烷氧基-四氟吡啶衍生物被用作合成14和16元大环系统的基础，所述大环系统包括吡啶和聚醚或胺亚基；X射线晶体学表征了两个大环。
• Preparation, characterization and use of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an eco-benign, efficient and reusable ionic liquid catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups
  作者：Nader Ghaffari Khaligh

  DOI：10.1016/j.molcata.2011.08.021

  日期：2011.10

  New and novel ionic liquid (3-methyl-1-sulfonic acid imidazolium hydrogen sulfate) is a recyclable and eco-benign catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups under solvent-free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-8 min). The catalyst was characterized by FT-IR, H-1 NMR and C-13 NMR studies. All the products were extensively characterized by H-1 NMR, IR, GC-MS and melting point analyses. A mechanism for the catalytic activity is proposed. The catalyst can be recovered and reused 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) 2011 Elsevier B.V. All rights reserved.

表征谱图