Me(CH2)4CH(OSiMe3)Me | 53690-75-8

• 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: Me(CH2)4CH(OSiMe3)Me
• 英文别名: CH3(CH2)4CH(OSiMe3)CH3；CH3(CH2)4CH2(OSiMe3)CH3；Silane, trimethyl[(1-methylhexyl)oxy]-；heptan-2-yloxy(trimethyl)silane
• CAS: 53690-75-8
• 化学式: C₁₀H₂₄OSi
• 分子量: 188.385
• InChiKey: ARLOCEWCOYNVON-UHFFFAOYSA-N

物化性质

• 沸点：
  188.3±8.0 °C(Predicted)
• 密度：
  0.797±0.06 g/cm3(Predicted)
• 保留指数：
  1008.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• 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：

  Me(CH2)4CH(OSiMe3)Me 在 γ-picolinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到2-庚酮
  参考文献：
  名称：

  摘要：

  Deprotection of cyclic acetals and oxidative desilylation of trimethylsilyl ethers into the corresponding carbonyl compounds with gamma-picolinium chlorochromate (gamma-PCC) under nonaqueous conditions at room temperature is described. Oxidation of aldehydes to carboxylic acids was not observed in any case.

  DOI：

  10.1023/a:1022526521167
• 作为产物：
  描述：

  2-庚酮 以1%的产率得到
  参考文献：
  名称：

  HUDRLIK P. F.; TAKACS J. M., J. ORG. CHEM., 1978, 43, NO 20, 3861-3865

  摘要：

  DOI：

文献信息

• <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。
• A novel and highly efficient method for the silylation of alcohols with hexamethyldisilazane (HMDS) catalyzed by recyclable sulfonic acid-functionalized ordered nanoporous silica
  作者：Daryoush Zareyee、Babak Karimi

  DOI：10.1016/j.tetlet.2006.12.030

  日期：2007.2

  Silylation of alcohols with hexamethyldisilazane (HMDS) in dichloromethane provides the corresponding silyl ethers in almost quantitative yields at room temperature using 1–3 mol % of sulfonic acid-functionalized silica. Additionally, the catalyst displays a high activity and thermal stability (up to 240 °C) and it can be easily recovered and reused for at least 20 reaction cycles without loss of reactivity

  在室温下，使用1-3 mol％的磺酸官能化二氧化硅，可以将醇与六甲基二硅氮烷（HMDS）进行甲硅烷基化，从而以几乎定量的产率提供相应的甲硅烷基醚。另外，该催化剂显示出高活性和热稳定性（高达240°C），并且可以容易地回收和再利用至少20个反应周期，而不会损失反应活性。
• A New and Efficient Method for the Protection of Alcohols and Phenols by Using Hexamethyldisilazane in the Presence of Anhydrous Ferric Chloride under Mild Reaction Conditions
  作者：Batool Akhlaghinia

  DOI：10.1080/10426500601047487

  日期：2007.4.1

  Alcohols and phenols are protected with hexamethyldisilazane in the presence of anhydrous ferric chloride in good to excellent yields in acetonitrile. This method is highly selective for the conversion of primary alcohols in the presence of secondary and tertiary alcohols and also for conversion phenols.

  醇和酚在无水氯化铁存在下用六甲基二硅氮烷保护，在乙腈中的收率良好至极好。该方法对于在仲醇和叔醇存在下伯醇的转化以及酚类的转化具有高度选择性。
• <i>p</i>-Toluenesulfonyl Chloride (<i>p</i>-TsCl)-Catalyzed Trimethylsilylation of Hydroxyl Groups Using Hexamethyldisilazane and Their Regeneration Under Mild Conditions: The First Example for Catalytic Application of <i>p</i>-Toluenesulfonyl Chloride
  作者：Ardeshir Khazaei、Amin Rostami、Fatemeh Mantashlo

  DOI：10.1080/10426500802453872

  日期：2009.9.18

  The first catalytic application of p-toluenesulfonyl chloride (p-TsCl) for the efficient and selective trimethylsilylation of various types of hydroxyl groups with hexamethyldisilazane (HMDS) in dichloromethane and desilylation of these compounds in water is reported. The reactions were carried out at room temperature and were found to proceed in good to excellent yields.

  报道了对甲苯磺酰氯 (p-TsCl) 在二氯甲烷中与六甲基二硅氮烷 (HMDS) 对各种类型的羟基进行有效和选择性的三甲基甲硅烷基化以及这些化合物在水中的脱甲硅烷基化的首次催化应用。反应在室温下进行，发现以良好到极好的产率进行。
• 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。