三甲基-(2-苯基苯氧基)硅烷 | 1022-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 三甲基-(2-苯基苯氧基)硅烷
• 英文名称: trimethyl(biphenyl-2-yloxy)silane
• 英文别名: 2-PhC6H4OTMS；2-PhC6H4OH；2-trimethylsilanyloxy-biphenyl；biphenyl-2-yloxy-trimethyl-silane；Biphenyl-2-yloxy-trimethyl-silan；[([1,1'-Biphenyl]-2-yl)oxy](trimethyl)silane；trimethyl-(2-phenylphenoxy)silane
• CAS: 1022-21-5
• 化学式: C₁₅H₁₈OSi
• 分子量: 242.393
• InChiKey: GNXKFLQLCGNBMC-UHFFFAOYSA-N

物化性质

• 沸点：
  103.0-103.5 °C(Press: 1 Torr)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  三甲基-(2-苯基苯氧基)硅烷 在 甲醇 、 1,3-disulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.07h， 以99%的产率得到邻苯基苯酚
  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：

  邻苯基苯酚 、 六甲基二硅氮烷 在 [nano-MCM-41(at)(CH₂)3-1-methylimidazole]Br₃ 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以94%的产率得到三甲基-(2-苯基苯氧基)硅烷
  参考文献：
  名称：

  新型离子液体固定在MCM-41系统上用于六甲基二硅氮烷对醇和酚进行三甲基硅烷化的应用

  摘要：

  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。

  DOI：

  10.1007/s11164-018-3544-4

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，
• Silica-bonded<i>S</i>-sulfonic acid as a recyclable catalyst for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS)
  作者：Khodabakhsh Niknam、Dariush Saberi、Hajar Molaee、Mohammad Ali Zolfigol

  DOI：10.1139/v09-162

  日期：2010.2

  Silica-bonded S-sulfonic acid (SBSSA) was prepared by the reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in tert-butylmethyl ether, and used as a catalyst for the silylation of hy...

  由3-巯基丙基二氧化硅（MPS）与氯磺酸在叔丁基甲基醚中反应制备二氧化硅键合S-磺酸（SBSSA），用作甲硅烷基化的催化剂。
• 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
• P/O Ligand Systems: Facile Synthesis, Structure, and Catalytic Tests of 2′‐Phosphanyl‐1,1′ ‐phenyl‐2‐ols and 2′‐Phosphanyl‐1,1′‐binaphthyl‐2‐ols
  作者：Renat Kadyrov、Joachim Heinicke、Markus K. Kindermann、Detlef Heller、Christine Fischer、Rüdiger Selke、Axel K. Fischer、Peter G. Jones

  DOI：10.1002/cber.19971301118

  日期：1997.11

  A facile synthesis of 2′-phosphanyl-1,1′-biphenyl- and 2′-phosphanyl-1,1′ -binaphthyl-2-ols and their silyl ethers has been developed, consisting of electron-transfer-catalyzed ring-opening of dibenzofuran and dinaphthofuran, respectively, subsequent reaction with chlorophosphanes, and work-up with acetic acid or ClSiMe3. Studies of the molecular and crystal structures reveals the presence of P—H—O

  已开发了一种简便的合成方法，该方法由电子转移催化的开环组成，可轻松合成2'-膦酰基-1,1'-联苯-和2'-膦酰基-1,1'-联萘-2-醇及其甲硅烷基醚分别将二苯并呋喃和二萘并呋喃与氯膦反应，然后用乙酸或ClSiMe 3进行后处理。对分子和晶体结构的研究表明，在更基本的t BuPhP衍生物中存在PB桥键，而在联苯衍生物中芳基平面几乎垂直排列。在P不对称衍生物3d的情况下，通过NMR确定芳基平面绕CC轴旋转的势垒，通过对映异构和P不对称使用非对映异构体的出现。在均相Rh催化反应中对标题化合物，膦酰基苯酚和膦基萘酚的比较筛选测试表明，在加氢甲酰化反应中具有催化活性，并且联苯和联萘-2-醇衍生物相对于其他P-O配体而言具有优越的性能。
• Trimethylsilyl trichloroacetate: a new reagent for salt-free silylations
  作者：James M. Renga、Pen-Chung Wang

  DOI：10.1016/s0040-4039(00)98426-0

  日期：1985.1

  Trimethylsilyl trichloroacetate () is a convenient reagent for the silylation of phenols, carboxylic acids, mercaptans, amides, acetylenes, and β-keto esters, while the reaction of with aldehydes and ketones affords silylated trichloromethyl carbinols ().

  三氯乙酸三甲基甲硅烷基酯（）是用于苯酚，羧酸，硫醇，酰胺，乙炔和β-酮酯甲硅烷基化的便捷试剂，而与醛和酮的反应则可提供甲硅烷基化的三氯甲基甲醇（）。