(1-cyclohexylethoxy)trimethylsilane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1-cyclohexylethoxy)trimethylsilane
• 英文别名: 1-Cyclohexylethanol, TMS derivative；1-cyclohexylethoxy(trimethyl)silane
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: IZGUVSNDJWWEKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  (1-cyclohexylethoxy)trimethylsilane 在 水 、 硼酸 作用下， 反应 1.0h， 以90%的产率得到1-环己基乙醇
  参考文献：
  名称：

  Boric acid as cost-effective and recyclable catalyst for trimethylsilyl protection and deprotection of alcohols and phenols

  摘要：

  Boric acid has been used as a green, selective and recyclable catalyst for trimethysilylation of alcohols and phenols using hexamethyldisilazane in acetonitrile. Deprotection of trimethylsilyl ethers to their parent alcohols and phenols was also achieved using this catalyst in water at room temperature. The salient features of this methodology are cheap processing, mild acidity conditions, excellent yields of products and easy availability of the catalyst.

  DOI：

  10.1590/s0103-50532010000800026
• 作为产物：
  描述：

  1-环己基乙醇 、 六甲基二硅氮烷 在 ammonium cerium (IV) nitrate 、 potassium iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 以87%的产率得到(1-cyclohexylethoxy)trimethylsilane
  参考文献：
  名称：

  Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalysed by in situ generated I 2 using Oxone®/KI or cerium ammonium nitrate (CAN)/KI systems under mild conditions

  摘要：

  结构多样化的醇和酚在六甲基二硅氮烷（HMDS）存在下与由Oxone®/KI或CAN/KI体系原位生成的催化量碘进行的反应中，以清洁高效的方式进行了三甲基硅烷化。这些反应在室温下在湿润的氯仿中迅速进行，产率良好至高。

  DOI：

  10.1007/s12039-011-0120-5

文献信息

• H₅IO₆/KI: A New Combination Reagent for Iodination of Aromatic Amines, and Trimethylsilylation of Alcohols and Phenols through<i>in situ</i>Generation of Iodine under Mild Conditions
  作者：Mohammad Ali Zolfigol、Ardeshir Khazaei、Eskandar Kolvari、Nadiya Koukabi、Hamid Soltani、Maryam Behjunia

  DOI：10.1002/hlca.200900259

  日期：2010.3

  A simple method for the in situ generation of iodine using H5IO6/KI has been developed, and its application in silylation of OH group and iodination of aromatic amines is described.

  已开发出一种使用H 5 IO 6 / KI原位生成碘的简单方法，并描述了其在OH基甲硅烷基化和芳族胺碘化中的应用。
• <i>N</i>-Bromosuccinimide (NBS) — Selective and effective catalyst for trimethylsilylation of alcohols and phenols using hexamethyldisilazane and their regeneration under mild and neutral reaction conditions
  作者：Ardeshir Khazaei、Amin Rostami、Ayeh Raiatzadeh、Marjan Mahboubifar

  DOI：10.1139/v07-029

  日期：2007.5.1

  Structurally diverse alcohols and phenols were trimethylsilylated in a clean and efficient reaction with hexamethyldisilazane (HMDS) based on the use of a catalytic amount of N-bromosuccinimide under both dichloromethane and solvent-free conditions at room temperature. Deprotection of trimethylsilyl ethers was also be achieved efficiently in the presence of a catalytic amount of NBS in methanol at ambient temperature.Key words: N-bromosuccinimide, solvent-free, alcohols, phenols, hexamethyldisilazane, trimethylsilyl ether, catalyst, detrimethylsilylation.

  在室温下的二氯甲烷和无溶剂条件下，使用一定量的 N-溴代琥珀酰亚胺催化剂，通过与六甲基二硅氮烷（HMDS）进行清洁高效的反应，实现了结构多样的醇和酚的三甲基硅烷化。在催化量 NBS 的存在下，在室温下的甲醇中也能有效地实现三甲基硅基醚的脱保护：N-溴代丁二酰亚胺、无溶剂、醇、酚、六甲基二硅氮烷、三甲基硅基醚、催化剂、去甲基硅烷化。
• Novel and Highly Effective Method for the Trimethylsilylation of Alcohols and Phenols with Hexamethyldisilazane (HMDS), Catalyzed by I₂Generated<i>in situ</i>Using Fe(NO₃)₃⋅9 H₂O/NaI under Heterogeneous and Neutral Conditions
  作者：Ardeshir Khazaei、Sadegh Rahmati、Amin Rostami

  DOI：10.1002/hlca.200900002

  日期：2009.7

  Structurally diverse alcohols and phenols were trimethylsilylated in a clean and efficient reaction with hexamethyldisilazane (HMDS) based on the use of I2 generated in situ from Fe(NO3)3⋅9 H2O/NaI. The reaction occurs very rapid in good‐to‐high yield in CH2Cl2 at room temperature, and the use of toxic and corrosive molecular I2 is avoided.

  结构不同的醇和酚是在用六甲基二硅烷（HMDS）清洁和有效的反应基于使用的我三甲基甲硅烷2产生原位选自Fe（NO 3）3 ⋅9ħ 2 O /碘化钠。在室温下，该反应在CH 2 Cl 2中以高至高收率非常迅速地发生，并且避免使用有毒和腐蚀性的分子I 2。
• Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalysed by in situ generated I 2 using Oxone®/KI or cerium ammonium nitrate (CAN)/KI systems under mild conditions
  作者：Eskandar Kolvari、Ardeshir Khazaei、Mohammad Ali Zolfigol、Nadiya Koukabi、Maryam Gilandoust、Neda Bakhit

  DOI：10.1007/s12039-011-0120-5

  日期：2011.9

  Structurally diverse alcohols and phenols were trimethylsilylated in clean and efficient reactions with hexamethyldisilazane (HMDS) in the presence of a catalytic amount of I2 generated in situ from Oxone®/KI or CAN/KI systems. The reactions occur rapidly in good to high yields in wet CH2Cl2 at room temperature.

  结构多样化的醇和酚在六甲基二硅氮烷（HMDS）存在下与由Oxone®/KI或CAN/KI体系原位生成的催化量碘进行的反应中，以清洁高效的方式进行了三甲基硅烷化。这些反应在室温下在湿润的氯仿中迅速进行，产率良好至高。
• Salt-Free Preparation of Trimethylsilyl Ethers by B(C₆F₅)₃-Catalyzed Transfer Silylation by Using a Me₃SiH Surrogate
  作者：Antoine Simonneau、Jonas Friebel、Martin Oestreich

  DOI：10.1002/ejoc.201301840

  日期：2014.4

  promoted by the same boron catalyst. Benzene and dihydrogen are formed during the reaction, but no salt waste is. This expedient protocol is applicable to several silicon groups, and the preparation of trimethylsilyl ethers presented here is potentially useful for alcohol derivatization prior to GLC analysis.

  描述了由强路易斯酸 B(C6F5)3 催化的前所未有的醇转移硅烷化反应。气态 Me3SiH 由 B(C6F5)3 催化分解 3-三甲基甲硅烷基环己-1,4-二烯原位释放，随后与醇在相同硼催化剂促进的脱氢 Si-O 偶联中反应。在反应过程中形成苯和二氢，但没有盐废物。此权宜之计适用于多个硅基团，此处介绍的三甲基甲硅烷基醚的制备对于 GLC 分析之前的醇衍生化可能有用。