[(4-methoxyphenyl)methoxy]tris(propan-2-yl)silane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(4-methoxyphenyl)methoxy]tris(propan-2-yl)silane
• 英文别名: 4-triisopropylsilyloxymethyl(methoxy)benzene；4-MeOPhCH2OSi(i-Pr)3；(4-Methoxyphenyl)methoxy-tri(propan-2-yl)silane
• 化学式: C₁₇H₃₀O₂Si
• 分子量: 294.51
• InChiKey: JZWJWEIMGNUVRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  [(4-methoxyphenyl)methoxy]tris(propan-2-yl)silane 在 zinc trifluoromethanesulfonate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以90%的产率得到4-甲氧基苄醇
  参考文献：
  名称：

  使用三氟甲磺酸锌（II）对甲硅烷基醚进行简便，高效和化学脱保护

  摘要：

  背景：迄今为止，已经开发了许多用于羟基官能团的保护基。醇最常被保护为醚和酯，其中烷基和苄基醚是强保护基，而其他诸如THP，TBS，TPS和MEM / MOM醚则对酸不稳定。在所有其他羟基保护基中，甲硅烷基醚是最常用的保护基，因为它们易于安装且有效安装，并且对各种有用的试剂和反应条件稳定。在甲硅烷基醚中，三乙基甲硅烷基（TES），叔丁基二甲基甲硅烷基（TBDMS），三异丙基甲硅烷基（TIPS）和叔丁基二苯基甲硅烷基（TBDPS）部分是多步有机合成中常用的羟基保护基。 方法：一种温和，有效和选择性的方法，用于脱保护高产率开发的各种甲硅烷基醚，方法是在室温下在甲醇中使用20 mol％的三氟甲磺酸锌（II）（Zn（OTf）2）作为溶剂，而不影响两者报道了对酸和碱敏感的保护基。 结果：为了研究该方法的一般性，从具有不同保护基团的多种底物制备了几种甲硅烷基醚，并使用MeOH中的Zn（OTf）2对其进行甲硅烷基化。

  DOI：

  10.2174/1570178614666170710120051
• 作为产物：
  描述：

  三异丙基硅烷 、 4-甲氧基苄醇 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以69%的产率得到[(4-methoxyphenyl)methoxy]tris(propan-2-yl)silane
  参考文献：
  名称：

  叔丁醇钾催化脱氢的Si ？O耦合：酒精保护不足的反应性模式和机理

  摘要：

  就这么简单！钾叔丁醇单独催化直接脱氢的Si 的几个合成重要硅烷与1 O联接°，2°，甚至3°醇，而不需要化学计量的盐酸清除剂。立体固位机理是通过硅立体烷硅烷来探测的。

  DOI：

  10.1002/asia.200800426
• 作为试剂：
  描述：

  (4-甲氧基苯基)甲氧基三甲基硅烷 在 [(4-methoxyphenyl)methoxy]tris(propan-2-yl)silane 作用下， 以 乙腈 为溶剂， 反应 0.02h， 以90%的产率得到4-甲氧基苄醇
  参考文献：
  名称：

  Heterogeneous Thiocyanation of Benzylic Alcohols and Silyl and THP Ethers, and Deprotection of Silyl and THP-Ethers by [PCl_3-n(SiO₂)_n] (Silphos)

  摘要：

  Silicaphosphite (silphos), [PCl3-n(SiO2)n], as a heterogeneous phosphorous compound, catalyzes the thiocyanation of benzylic alcohols and silyl and THP ethers in the presence of I2 and NH4SCN in refluxing CH3CN. The produced silphos oxide byproduct can be easily separated by a simple filtration. Silphos is also used for the efficient and selective deprotection of silyl and THP-ethers to their corresponding alcohols.

  DOI：

  10.1080/10426500903419145

文献信息

• Efficient and Selective Protection of Alcohols and Phenols with Triisopropylsilyl Chloride/Imidazole Using Microwave Irradiation
  作者：Ali Khalafi-Nezhad、Reza Fareghi Alamdari、Negar Zekri

  DOI：10.1016/s0040-4020(00)00638-4

  日期：2000.9

  A very simple and efficient method is described for silylation of alcohols and phenols using triisopropylsilyl chloride and imidazole under microwave irradiation. High selectivity was observed for silylation of primary and secondary alcohols and also for structurally different phenols.

  描述了在微波辐射下使用三异丙基甲硅烷基氯和咪唑使醇和苯酚甲硅烷基化的非常简单和有效的方法。对于伯醇和仲醇的甲硅烷基化以及在结构上不同的苯酚，均观察到高选择性。
• Directed Lithiation in Arenetricarbonylchromium(0) Complexes: Assessment of Some Directing Group Specificities and of Electrophilic Quench Efficacies
  作者：Iyassu K. Sebhat、Yen-Ling Tan、David A. Widdowson、René Wilhelm、Andrew J.P. White、David J. Williams

  DOI：10.1016/s0040-4020(00)00562-7

  日期：2000.8

  The synthesis of a series of phenol ethers and 4-triisopropylsilyloxymethylphenol ethers and their η6-tricarbonylchromium(0) complexes are reported. The directed lithiation of these followed by quenching with a series of electrophiles gave access to a wide range of functionalised complexes for use in synthesis.

  一系列苯酚醚和4- triisopropylsilyloxymethylphenol醚及其η的合成6报告-tricarbonylchromium（0）配合物。将它们直接定向锂化，然后用一系列亲电试剂淬灭，可得到广泛的用于合成的功能化配合物。
• Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
  作者：Dominik Hager、David W. C. MacMillan

  DOI：10.1021/ja5102695

  日期：2014.12.10

  The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C-H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical-radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable.
• EFFECTIVE SILYLATION OF CARBOXYLIC ACIDS UNDER SOLVENT-FREE CONDITIONS WITH <i>tert</i>-BUTYLDIMETHYLSILYL CHLORIDE (TBDMSCL) AND TRIISOPROPYLSILYL CHLORIDE (TIPSCL)
  作者：Habib Firouzabadi、Naser Iranpoor、Hamid Reza Shaterian

  DOI：10.1080/10426500008076532

  日期：2000.1.1

  Various types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2 degrees, 3 degrees hydroxyl groups are observed.
• Palladium Nano-Dispersed and Stabilized in Organically Modified Silicate as a Heterogeneous Catalyst for the Conversion of Aldehydes into O-Silyl Ether Derivatives under Neat Conditions
  作者：Caitlyn M. Matherne、Jordan E. Wroblewski、Jean Fotie、Heather S. Drago、Gabriela T. Marchan、Alexis R. Young、Nkechi Kingsley、Craig P. Plaisance

  DOI：10.1055/a-2326-6277

  日期：2024.7

  Palladium nanoparticles are dispersed and stabilized in organically modified silicate (Pd@MTES), and characterized by a number of spectroscopic techniques, including FTIR, TEM, SEM, and XPS. The catalytic effect of this material toward the hydrosilylation of aldehydes and ketones is explored, and the scope of the reaction investigated, with 26 examples provided. This reaction proceeds under neat conditions via heterogeneous catalysis, and a mechanistic pathway supported by DFT calculations is proposed.