(9H-fluoren-9-ylmethoxy)trimethylsilane | 1162648-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-ylmethoxy)trimethylsilane
• CAS: 1162648-59-0
• 化学式: C₁₇H₂₀OSi
• 分子量: 268.431
• InChiKey: WDHUBBAPLDURTP-UHFFFAOYSA-N

物化性质

• 沸点：
  344.0±11.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-ylmethoxy)trimethylsilane 在 甲醇 、 vanadium hydrogen sulfate 作用下， 反应 0.08h， 以92%的产率得到9-芴甲醇
  参考文献：
  名称：

  硫酸氢钒 (I)：醇的化学选择性三甲基甲硅烷基化和三甲基甲硅烷基醚的脱保护

  摘要：

  报道了在温和且完全非均相的反应条件下，V(HSO 4 ) 3 催化醇与六甲基二硅氮烷 (HMDS) 的三甲基硅烷化反应。该方法对于在酚、胺和硫醇存在下保护醇具有高度的化学选择性。此外，三甲基甲硅烷基醚的脱保护是在室温下在 V(HSO 4 ) 3 存在下以良好至高产率进行的。

  DOI：

  10.1002/jccs.200800140
• 作为产物：
  描述：

  9-芴甲醇 、 六甲基二硅氮烷 在 poly(4-vinylpyridine) 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以98%的产率得到(9H-fluoren-9-ylmethoxy)trimethylsilane
  参考文献：
  名称：

  Poly(4-vinylpyridine) catalyzed chemoselective O-TMS protection of alcohols and phenols and N-Boc protection of amines

  摘要：

  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。

  DOI：

  10.1007/s13738-011-0060-5

文献信息

• Rapid and Efficient Trimethylsilyl Protection of Hydroxyl Groups Catalyzed by Niobium(V) Chloride
  作者：Jun-Tao Hou、Hong-Li Chen、Zhan-Hui Zhang

  DOI：10.1080/10426507.2010.482544

  日期：2010.12.30

  variety of alcohols, including primary, benzylic, secondary, and phenols with hexamethyldisilazane, has been developed. The reactions were carried out at room temperature in the presence of a catalytic amount of niobium(V) chloride and afforded the corresponding trimethylsilyl ethers in high to excellent yields in short time. GRAPHICAL ABSTRACT

  摘要 已经开发了一种高效、方便的方法，用于使用六甲基二硅氮烷对包括伯醇、苄醇、仲醇和酚在内的多种醇进行三甲基硅烷化。该反应在室温下在催化量的氯化铌 (V) 存在下进行，并在短时间内以高至极好的收率提供相应的三甲基甲硅烷基醚。图形概要
• Introduction of PEG-SANM nanocomposite as a new and highly efficient reagent for the promotion of the silylation of alcohols and phenols and deprotection of the silyl ethers
  作者：Farhad Shirini、Abdollah Fallah Shojaei、Seyedeh Zahra Dalil Heirati

  DOI：10.1080/10426507.2015.1119141

  日期：2016.6.2

  was prepared by a simple method and characterized using XRD, TGA, SEM, TEM, and FT-IR techniques. After preparation and characterization, this reagent was used as a highly efficient and reusable solid acid catalyst for the chemoselective silylation of alcohols and phenols and deprotection of the obtained silyl ethers. The method offers several advantages including high to excellent yields of the products

  图形摘要 摘要 聚（乙二醇）-磺化蒙脱石钠 (PEG-SANM) 纳米复合材料是通过一种简单的方法制备的，并使用 XRD、TGA、SEM、TEM 和 FT-IR 技术进行表征。经过制备和表征，该试剂被用作高效、可重复使用的固体酸催化剂，用于醇和酚的化学选择性甲硅烷基化和所得甲硅烷基醚的脱保护。该方法具有多种优点，包括产物的收率高至极好、反应时间短、催化剂易于制备和后处理程序简单。此外，催化剂至少可以循环使用5次，催化活性不会明显下降。
• Preparation and characterization of a RHA/TiO₂nanocomposite: introduction of an efficient and reusable catalyst for chemoselective trimethylsilyl protection and deprotection of alcohols and phenols
  作者：Mohadeseh Seddighi、Farhad Shirini、Omid Goli-Jolodar

  DOI：10.1039/c5ra26607f

  日期：——

  nanoparticles leading to the RHA/TiO2 nanocomposite. This nanocomposite was used as an efficient catalyst for the chemoselective trimethylsilylation of various alcohols and phenols and deprotection of the obtained trimethylsilyl ethers. The procedure gave the products in excellent yields in very short reaction times. Also this catalyst can be reused at least six times without loss of its catalytic activity.

  在这项工作中，稻壳灰（RHA）作为无定形二氧化硅的天然来源，被用作合成RHA / TiO 2纳米复合材料的锐钛矿相二氧化钛纳米粒子的载体。该纳米复合材料用作各种醇和酚的化学选择性三甲基甲硅烷基化和所得三甲基甲硅烷基醚的脱保护的有效催化剂。该程序在非常短的反应时间内以优异的产率获得了产物。同样，该催化剂可以重复使用至少六次，而不会损失其催化活性。
• Chemoselective trimethylsilylation of alcohols catalyzed by saccharin sulfonic acid
  作者：Farhad Shirini、Mohammad Ali Zolfigol、Masoumeh Abedini

  DOI：10.1007/s00706-008-0004-7

  日期：2009.1

  Saccharin sulfonic acid was easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This reagent is efficiently able to catalyze the chemoselective trimethylsilylation of alcohols with hexamethyldisilazane in the presence of amines and thiols.
• Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
  作者：Marjan Jereb

  DOI：10.1016/j.tet.2012.03.040

  日期：2012.5

  An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol%) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process. (C) 2012 Elsevier Ltd. All rights reserved.