trimethyl [2-(benzylamino)ethoxy]silane

• 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 [2-(benzylamino)ethoxy]silane
• 英文别名: N-benzyl-2-trimethylsilyloxyethanamine
• 化学式: C₁₂H₂₁NOSi
• 分子量: 223.39
• InChiKey: RLKUNSPAZCMYJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trimethyl [2-(benzylamino)ethoxy]silane 在 甲醇 、 1,3-disulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.07h， 以97%的产率得到N-苄基乙醇胺
  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：

  三甲基硅咪唑 、 N-苄基乙醇胺 以 二氯甲烷 为溶剂， 生成 trimethyl [2-(benzylamino)ethoxy]silane
  参考文献：
  名称：

  来自氨基醇的三氟乙酰胺作为亲核三氟甲基化试剂。

  摘要：

  DOI：

  10.1002/anie.200351301

文献信息

• Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
  作者：Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah、Ali-Reza Aliakbar

  DOI：10.1016/j.crci.2013.01.018

  日期：2014.2

  eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively

  摘要 以稻壳 (RiH) 为原料，开发了一种温和、高效、环保的方案，用于化学选择性保护苄基和伯和受阻较小的仲脂肪醇和酚作为三甲基甲硅烷基醚以及不同类型的胺作为 N-叔丁基氨基甲酸酯。催化剂。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。该方法的显着特点是后处理简单、反应时间相对较短、收率高、成本低、催化剂的可用性和可重复使用性是该方法的显着特点，可被认为是保护醇、酚的最佳和通用方法之一、硫醇和胺。此外，
• Rice Husk Ash: A New, Cheap, Efficient, and Reusable Reagent for the Protection of Alcohols, Phenols, Amines, and Thiols
  作者：F. Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah

  DOI：10.1080/10426507.2013.844142

  日期：2014.5.4

  Abstract A mild, efficient, and eco-friendly protocol for the protection of alcohols and phenols as trimethylsilyl ethers has been developed using rice husk ash as a reagent. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols, and amines with acetic anhydride. All reactions were performed under mild conditions in good to high yields. [Supplementary materials are available

  摘要 以稻壳灰为试剂，开发了一种温和、高效、环保的三甲基甲硅烷基醚类醇类和酚类保护方案。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。所有反应均在温和条件下以良好至高产率进行。[本文提供补充材料。访问出版商的在线版磷、硫和硅及相关元素，获取以下免费补充文件：附加文本、表格和数字。] 图形摘要
• 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。
• Nanoporous Na⁺-Montmorillonite Perchloric Acid as an Efficient and Recyclable Catalyst for the Chemoselective Protection of Hydroxyl Groups
  作者：Maryam Mashhadinezhad、Farhad Shirini、Manouchehr Mamaghani

  DOI：10.1166/jnn.2019.15524

  日期：2019.4.1

  X-ray spectroscopy (EDX), pH analysis and determination of the Hammett acidity function. The prepared reagent showed excellent catalytic activity for the chemoselective conversion of alcohols and phenols to their corresponding trimethylsilyl ethers with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Deprotection of the resulting trimethylsilyl ethers can also be carried out using the same

  通过将Na +-蒙脱石作为高价酸的便宜且可商购的载体进行处理，可以轻松地制备出纳米多孔Na +-蒙脱石高氯酸作为一种新型的多相可重复使用的固体酸催化剂。使用多种技术对催化剂进行了表征，包括X射线粉末衍射（XRD），傅里叶变换红外光谱（FTIR），扫描电子显微镜（SEM），热重分析（TGA），能量色散X射线光谱（EDX）， pH分析和Hammett酸度功能的测定。所制备的试剂在室温下对醇和酚与1,1,1,3,3,3-六甲基二硅氮烷（HMDS）的化学选择性转化为其相应的三甲基甲硅烷基醚显示出优异的催化活性。所得的三甲基甲硅烷基醚的脱保护也可以使用相同的催化剂在乙醇中进行。所有反应均在温和且完全异质的反应条件下以良好至极好的收率进行。该方案的显着优点是：反应时间短，产率高，试剂的可获得性和成本低，易于处理的过程以及在简单过滤过程中催化剂的可重复使用性。
• 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.