Borneol, trimethylsilyl ether | 74472-21-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Borneol, trimethylsilyl ether
• 英文别名: trimethyl-[(1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl)oxy]silane
• CAS: 74472-21-2；37555-29-6；37555-30-9；88390-69-6
• 化学式: C₁₃H₂₆OSi
• 分子量: 226.434
• InChiKey: RUVRGUBFCPLVCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 20 Torr)
• 密度：
  0.8955 g/cm3(Temp: 16 °C)
• 保留指数：
  1234.2

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Borneol, trimethylsilyl ether 在 silica triflate 作用下， 以 甲醇 为溶剂， 反应 0.07h， 以90%的产率得到borneol
  参考文献：
  名称：

  三氟甲磺酸硅作为一种新型、高效、可重复使用的试剂，用于醇和酚的化学选择性硅烷化和甲硅烷基醚的脱保护

  摘要：

  硅胶与三氟甲磺酰氯在室温下反应很容易制备三氟甲磺酸二氧化硅。该化合物可用作有效且可重复使用的试剂，用于在溶液中和无溶剂条件下对醇和酚进行化学选择性甲硅烷基化。该试剂还有效地催化了回流甲醇中甲硅烷基醚的脱保护。

  DOI：

  10.1080/10426500701567046
• 作为产物：
  描述：

  borneol 、 六甲基二硅氮烷 在 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.08h， 以90%的产率得到Borneol, trimethylsilyl ether
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.molcata.2011.08.021

文献信息

• PROTECTION OF ALCOHOLS AND ACIDS WITH ALLYLSILANES CATALYZED BY IODINE OR IODOTRIMETHYLSILANE IN CHLORINATED HYDROCARBON
  作者：Akira Hosomi、Hideki Sakurai

  DOI：10.1246/cl.1981.85

  日期：1981.1.5

  Many triorganosilyl ethers and esters were prepared by the reaction of allylsilanes with alcohols catalyzed by iodine or iodotrimethylsilane in excellent yields. Bromine and bromotrimethylsilane were also effective catalysts.

  许多三有机甲硅烷基醚和酯是通过烯丙基硅烷与醇在碘或碘三甲基硅烷的催化下以优异的产率反应制备的。溴和溴三甲基硅烷也是有效的催化剂。
• Lakouraj; Akbari, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 5, p. 1165 - 1167
  作者：Lakouraj、Akbari

  DOI：——

  日期：——
• Cu(NO₃)₂ · 3 H₂O as an Efficient Reagent for the Chemoselective Trimethylsilylation of Primary Alcohols and Oxidation of Trimethylsilyl Ethers
  作者：F. Shirini、M. Mashhadi-Nejad

  DOI：10.1080/10426507.2011.614300

  日期：2012.3.1

  Cu(NO3)(2) center dot 3 H2O can be used as an efficient reagent for the chemoselective trimethylsilylation of primary benzylic and aliphatic alcohols with hexamethyldisilazane (HMDS). This reagent is also able to oxidize the obtained trimethylsilyl ethers to the corresponding carbonyl compounds in the presence of wet SiO2 and KBr. In this study, all reactions are performed in the absence of a solvent and good-to-high yields are obtained.
• Nanocrystalline TiO2–HClO4 as a new, efficient and recyclable catalyst for the chemoselective trimethylsilylation of alcohols, phenols and deprotection of silyl ethers
  作者：Farhad Shirini、Seyyed Vahid Atghia、Mojtaba Ghazi Jirdehi

  DOI：10.1016/j.catcom.2011.11.002

  日期：2012.2

  TiO2-HCIO4, as a new solid acid, was found to be an efficient catalyst for the chemoselective trimethylsilylation of alcohols and phenols. Deprotection of the resulting trimethylsilylethers was achieved using the same catalyst in methanol solvent. The synthesized catalyst was characterized by FT-IR, SEM, TEM, BET and XRD analyses. Our novel synthetic method has the advantages of high yields, short reaction times, low cost and recyclability of the catalyst, simplicity and easy work-up compared to the conventional methods reported in the literature. (C) 2011 Elsevier B.V. All rights reserved.
• Efficient O-Trimethylsilylation of Alcohols and Phenols with Trimethylsilyl Azide Catalyzed by Tetrabutylammonium Bromide under Neat Conditions
  作者：David Amantini、Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo015814s

  日期：2001.10.1

  A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol %) of tetrabutylammonium bromide (TBABr) at 30 or 70 degreesC. Under catalytic conditions, the yields of the corresponding trimethylsilyl ethers were greater than 91%. This procedure also allows the selective protection of primary and secondary alcohols in the presence of tertiary ones.