2-HOC6H4CH2OSiMe3 | 212709-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-HOC6H4CH2OSiMe3
• 英文别名: 2-(Trimethylsilyloxymethyl)phenol
• CAS: 212709-00-7
• 化学式: C₁₀H₁₆O₂Si
• 分子量: 196.321
• InChiKey: NFYNNNUVFLPGNK-UHFFFAOYSA-N

物化性质

• 沸点：
  249.2±15.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-HOC6H4CH2OSiMe3 在 modified polyacrylamide-supported chlorochromate 作用下， 以 环己烷 为溶剂， 反应 6.0h， 以85%的产率得到水杨醛
  参考文献：
  名称：

  改性聚丙烯酰胺负载的氯铬酸盐作为新型高分子氧化剂

  摘要：

  合成了改性聚丙烯酰胺负载的氯铬酸盐，并用作通用且有效的氧化剂，用于氧化各种有机化合物，例如羟基化合物，甲硅烷基醚，肟，硫醇等。用该氧化剂未观察到产物过度氧化（醛成羧酸）。氧化剂不溶于氧化介质，氧化反应后铬（VI）离子牢固地结合在不溶的聚合物载体上。这种新型的聚合型氯代铬酸盐试剂的优点包括温和的反应条件，简便的后处理，较短的反应时间，试剂的可再生性以及易于制备和处理的优点。

  DOI：

  10.2298/jsc110131216t
• 作为产物：
  描述：

  水杨醇 在 12-tungstophosphoric acid immobilized on [bmim][FeCl₄] 作用下， 反应 0.05h， 生成 2-HOC6H4CH2OSiMe3
  参考文献：
  名称：

  H3PW12O40@[bmim][FeCl4]: A green catalytic system for alkoxymethylation of alcohols and their one-pot interconversion to acetates and TMS-ethers

  摘要：

  12-Tungstophosphoric acid immobilized on [bmim][FeCl4] was found to be an efficient catalyst for chemoselective methoxymethylation and ethxoymethylation of alcohols and also one-pot conversion of MOM- or EOM-ethers to their corresponding acetates and TMS-ethers under thermal conditions and microwave irradiation. These procedures were simple, rapid and the corresponding products were obtained in high yields. The catalyst exhibited remarkable reactivity and was reusable.

  DOI：

  10.1007/bf03249085

文献信息

• 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。
• Room temperature silylation of alcohols catalyzed by metal organic frameworks
  作者：Amarajothi Dhakshinamoorthy、Andrea Santiago-Portillo、Patricia Concepción、José R. Herance、Sergio Navalón、Mercedes Alvaro、Hermenegildo Garcia

  DOI：10.1039/c7cy00834a

  日期：——

  The commercial Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylic acid) metal organic framework (Basolite A100) is a suitable heterogeneous catalyst for the silylation of benzylic and aliphatic alcohols by hexamethyldisilazane in toluene at room temperature. Al(OH)(BDC) is stable under the reaction conditions as evidenced by powder XRD and can be reused with minimal activity decrease.

  商业化的Al（OH）（BDC）（BDC：1,4-苯二甲酸）金属有机骨架（Basolite A100）是一种适合的非均相催化剂，用于在室温下甲苯中六甲基二硅氮烷对苄基和脂族醇进行甲硅烷基化。粉末XRD证明Al（OH）（BDC）在反应条件下是稳定的，可以在活性降低最小的情况下重复使用。
• Microwave-assisted rapid and efficient deprotection and direct esterification and silylation of MOM and EOM ethers catalyzed by [Hmim][HSO4] as a Brønsted acidic ionic liquid
  作者：Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Ahmad Reza Khosropour、Arsalan Mirjafari

  DOI：10.1007/s00706-010-0373-6

  日期：2010.10

  Abstract1-Methylimidazolium hydrogensulfate, [Hmim][HSO4], a Brønsted acidic room temperature ionic liquid, is used as a catalyst and reaction medium for facile and eco-friendly deprotection of methoxymethyl (MOM) and ethoxymethyl (EOM) ethers to their corresponding alcohols under thermal conditions (Δ) and microwave irradiation (MW). Furthermore, one-pot interconversion to the respective acetates and

  摘要布朗斯台德酸性室温离子液体1-甲基咪唑硫酸氢盐[Hmim] [HSO 4 ]被用作催化剂和反应介质，可对甲氧基甲基（MOM）和乙氧基甲基（EOM）醚进行简便且环保的脱保护醇在热条件（Δ）和微波辐射（MW）下。此外，还实现了一锅转化为各自的乙酸酯和三甲基甲硅烷基（TMS）醚。 图形概要
• Rapid and efficient protection of alcohols and phenols, and deprotection of trimethylsilyl ethers catalyzed by a cerium-containing polyoxometalate
  作者：Bahram Yadollahi、Valiollah Mirkhani、Shahram Tangestaninejad、Davud Karimian

  DOI：10.1002/aoc.1715

  日期：2011.2

  convenient way for protection‐deprotection of alcohols in the presence of ammonium decatungstocerate(IV) (NH4)8[CeW10O36]·20H2O} as catalyst under ambient temperature in CH3CN. Using 0.002 mmol of the catalyst, various alcohols and phenols were transformed easily to the corresponding TMS ethers in excellent yields. In the second part, various TMS ethers were successfully converted to the parent hydroxyl

  在此，我们要报告一种简单便捷的方法，用于在环境温度下以CH为催化剂的去catungstocerate（IV）（NH 4）8 [CeW 10 O 36 ]·20H 2 O}铵存在下对醇进行保护-脱保护。3 CN。使用0.002 mmol的催化剂，各种醇和酚都可以轻松转化为相应的TMS醚，收率很高。在第二部分中，将多种TMS醚成功地转化为母体羟基化合物。版权所有©2010 John Wiley＆Sons，Ltd.
• Protection of alcohols in the presence of a new nano-sized DABCO-based ionic liquid catalyst containing zinc cation
  作者：Pouran Pourayoob Foumani、Maryam Mousapour、Farhad Shirini、Hassan Tajik、Shahed Hassanpoor

  DOI：10.1007/s13738-023-02928-1

  日期：2024.2

  performance of the prepared reagent was studied in the protection of alcohols in two ways using HMDS and DHP to obtain trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers, respectively. Solvent-free conditions, recoverability of the catalyst, use of low-cost starting materials, proper reaction times, high isolated yields and simple work-up procedure are among the most important features of this catalytic

  在目前的研究中，一种纳米路易斯酸性催化剂被命名为1,1ˊ-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium)-bis-zinc( II)三氯化物是通过ZnCl 2与[C 4 (DABCO) 2 ].2Cl的简单反应制备的，并通过FT-IR（傅立叶变换红外光谱）、TGA（热重分析）、XRD（X-射线粉末衍射）、SEM（扫描电子显微镜）、ICP-OES（电感耦合等离子体发射光谱仪）和 EDX（能量色散 X 射线）分析。然后，利用HMDS和DHP两种方式研究了所制备的试剂在醇保护中的催化性能，分别得到三甲基硅基(TMS)和四氢吡喃基(THP)醚。无溶剂条件、催化剂的可回收性、低成本原材料的使用、适当的反应时间、高分离产率和简单的后处理程序是该催化方法的最重要特征。