1,2-bis(trimethylsilyloxy)benzene | 5075-52-5

• 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: 1,2-bis(trimethylsilyloxy)benzene
• 英文别名: 1,2-benzenediol bis(trimethylsilyl) ether；pyrocatechol bis(trimethylsilyl) ether；1,2-bis(trimethylsiloxy)benzene；1,2-bis-trimethylsilanyloxy-benzene；[1,2-phenylenebis(oxy)]bis[trimethyl-silane]；1,2-bis(trimethylsiloxy)-benzene；Silane, (o-phenylenedioxy)bis[trimethyl-；trimethyl-(2-trimethylsilyloxyphenoxy)silane
• CAS: 5075-52-5
• 化学式: C₁₂H₂₂O₂Si₂
• 分子量: 254.476
• InChiKey: GEHYZCCVQVOFAF-UHFFFAOYSA-N

物化性质

• 保留指数：
  1309;1305;1322

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  1,2-bis(trimethylsilyloxy)benzene 在 甲醇 、 1,3-disulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.07h， 以98%的产率得到邻苯二酚
  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：

  邻苯二酚 生成 1,2-bis(trimethylsilyloxy)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

• [SnIV(TPP)(BF4)2]: An efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane
  作者：Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Shadab Gharaati

  DOI：10.1016/j.poly.2009.07.008

  日期：2010.1

  at room temperature. While, under the same reaction conditions [Sn IV (TPP)Cl 2 ] is less efficient to catalyze these reactions. One important feature of this catalyst is its ability in the chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.

  摘要锡（IV）四苯基卟啉四氟硼酸酯[Sn IV（TPP）（BF 4）2]被用作有效的催化剂，用于醇和酚与六甲基二硅氮烷（HMDS）的三甲基甲硅烷基化。高价[Sn IV（TPP）（BF 4）2]催化伯，仲和叔醇以及苯酚的三甲基硅烷化反应，在室温下以高收率和较短的反应时间获得了相应的TMS-醚。而在相同的反应条件下，[Sn IV（TPP）Cl 2]催化这些反应的效率较低。该催化剂的一个重要特征是它在仲，叔醇和酚存在下伯醇的化学选择性甲硅烷基化的能力。将该催化剂重复使用几次，而不会损失其催化活性。
• Highly efficient and selective trimethylsilylation of alcohols and phenols with hexamethyldisilazane catalyzed by polystyrene-bound tin(IV) porphyrin
  作者：Shadab Gharaati、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork

  DOI：10.1016/j.poly.2012.01.011

  日期：2012.3

  [Sn IV (TNH 2 PP)(OTf) 2 ], supported on chloromethylated polystyrene in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane is reported. The prepared catalyst was characterized by elemental analysis, FT-IR and diffuses reflectance UV–Vis spectroscopic methods. This catalyst was used for selective trimethylsilylation of different alcohols and phenols with HMDS, with short reaction

  摘要本文研究了氯甲基化聚苯乙烯负载的三（对氨基苯基）卟啉毒素（Sn IV（TNH 2 PP）（OTf）2）四（对氨基苯基）卟啉毒素（IV）的催化活性报道了六甲基二硅氮烷。所制备的催化剂通过元素分析，傅立叶变换红外（FT-IR）和漫反射紫外可见光谱法进行了表征。该催化剂用于用HMDS对不同的醇和酚进行选择性三甲基甲硅烷基化反应，反应时间短，收率高。该催化剂还具有高的可重复使用性和稳定性，因为它被回收了数次而没有损失其初始活性。
• Highly efficient and chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable electron-deficient [TiIV(salophen)(OTf)2]
  作者：Maryam Yadegari、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork

  DOI：10.1016/j.poly.2011.09.023

  日期：2012.1

  highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by high-valent [TiIV(salophen)(OTf)2] is reported. Under these conditions, primary, secondary and tertiary alcohols as well as phenols were silylated in short reaction times and high yields. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence

  在当前的工作中，报道了由高价[Ti IV（salophen）（OTf）2 ]催化的醇和酚与六甲基二硅氮烷（HMDS）的高效三甲基甲硅烷基化。在这些条件下，伯，仲和叔醇以及苯酚在较短的反应时间和高收率下被甲硅烷基化。值得注意的是，该方法可用于在仲，叔醇和酚存在下伯醇的化学选择性甲硅烷基化。将该催化剂重复使用几次，而不会损失其催化活性。
• Montmorillonite Clay Catalysis XI¹: Protection and Deprotection of Hydroxyl Group by Formation and Cleavage of Trimethylsilyl Ethers Catalysed by Montmorillonite K-10
  作者：Zhan-Hui Zhang、Tong-Shuang Li、Feng Yang、Cheng-Guang Fu

  DOI：10.1080/00397919808004891

  日期：1998.8

  Abstract An easy preparation of trimethylsilyl ethers of alcohols and phenols with 1,1,1,3,3,3-hexamethyldisilazane(HMDS) catalysed by montmorillonite K-10 at room temperature has been carried out in excellent yields. Desilyation of trimethylsilyl ethers is catalysed by K-10 in methanol at ambient temperature in high yields.

  摘要 以蒙脱石 K-10 为载体，在室温下以 1,1,1,3,3,3-六甲基二硅氮烷 (HMDS) 为原料制备了醇和酚的三甲基甲硅烷基醚，收率良好。三甲基甲硅烷基醚的脱甲硅烷基化反应在室温下由甲醇中的 K-10 以高产率催化。
• Poly(4-vinylpyridine) catalyzed chemoselective O-TMS protection of alcohols and phenols and N-Boc protection of amines
  作者：Farhad Shirini、Nader Ghaffari Khaligh

  DOI：10.1007/s13738-011-0060-5

  日期：2012.8

  Poly(4-vinylpyridine) (PVP) acts as an efficient and reusable catalyst for the selective and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and N-tert-butoxycarbonylation of amines with (Boc)2O. All reactions were performed under mild conditions in good to high yields.

  多（4-乙烯基吡啶）（PVP）作为选择性和高效的三甲基硅烷化醇和酚与六甲基二硅氮烷（HMDS）以及胺的N-叔丁氧羰基化与双（叔丁氧羰基）氧化物（Boc）2O的催化剂，具有高效和可重复使用的特性。所有反应都在温和条件下进行，产率为良好至高水平。

表征谱图