[(3-Chlorobenzyl)oxy]trimethylsilane | 1309880-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3-Chlorobenzyl)oxy]trimethylsilane
• 英文别名: 3-Chlorobenzyl alcohol, TMS derivative；(3-chlorophenyl)methoxy-trimethylsilane
• CAS: 1309880-47-4
• 化学式: C₁₀H₁₅ClOSi
• 分子量: 214.767
• InChiKey: KTQAQQDGBWYRMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(3-Chlorobenzyl)oxy]trimethylsilane 在 三氯异氰尿酸 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 3-氯二氯甲基苯
  参考文献：
  名称：

  使用三氯异氰尿酸和三苯膦作为有效的中性体系，将一锅的氧化和选择性的苄基甲硅烷基和四氢吡喃基醚转化为宝石二氯化物

  摘要：

  抽象的 首次描述了一种一锅法和氧化法，用于在中性介质中使用三氯异氰尿酸（TCCA）和三苯基膦（PPh 3）将苄基三甲基甲硅烷基（TMS）和四氢吡喃基（THP）醚转化为二氯化宝石。可以将包含吸电子或供电子基团的各种这些基材有效地转化成其相应的宝石-二氯化物，产率高至优异。本方法显示出高度的化学选择性，并且由于其一锅法性质符合绿色化学。

  DOI：

  10.1080/10426507.2020.1845680
• 作为产物：
  描述：

  3-氯苯甲醇 、 六甲基二硅氮烷 在 propyl sulfonic acid functionalized nanostructured SBA-15 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到[(3-Chlorobenzyl)oxy]trimethylsilane
  参考文献：
  名称：

  Silylation of Alcohols and Phenols with Hexamethyldisilazane over Highly Reusable Propyl Sulfonic Acid Functionalized Nanostructured SBA-15

  摘要：

  Various alcohols and phenols were trimethylsilylated in excellent yields using hexamethyldisilazane in the presence of catalytic amounts of environmentally friendly, hydrophobic, highly thermal stable, and completely heterogeneous sulfonic acid functionalized mesostructured SBA-15 in dichloromethane at ambient temperature. Primary, bulky secondary, tertiary, and phenolic hydroxyl functional groups were transformed to the corresponding trimethylsilyl ethers in excellent yields. The simple experimental procedure was accompanied by easy recovery and the catalyst was reusable (at least 18 reaction cycles); these are attractive features of this protocol.

  DOI：

  10.1016/s1872-2067(10)60300-2

文献信息

• Sulfonated Ordered Nanoporous Carbon (CMK-5-SO3H) as an Efficient and Highly Recyclable Catalyst for the Silylation of Alcohols and Phenols with Hexamethyldisilazane (HMDS)
  作者：Daryoush Zareyee、Mohammad S. Ghandali、Mohammad A. Khalilzadeh

  DOI：10.1007/s10562-011-0621-3

  日期：2011.10

  An environmentally friendly catalytic system for trimethylsilylation of alcohols and phenols with hexamethyldisilazane can be successfully carried out for the first time over sulfonated mesoporous carbon catalyst (CMK-5-SO3H) in dichloromethane at ambient temperature and excellent conversions were obtained. Furthermore, the catalyst displays high activity and thermal stability (to 200 A degrees C) and it can be reused repeatedly for at least 25 cycles without any evidence of loss of activity, confirming the stability of covalent bonding of acidic centers.
• Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid
  作者：Ghasem Aghapour、Zeinab Abbaszadeh

  DOI：10.1080/10426507.2014.990015

  日期：2015.9.2

  Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.
• Silylation of Alcohols and Phenols with Hexamethyldisilazane over Highly Reusable Propyl Sulfonic Acid Functionalized Nanostructured SBA-15
  作者：Daryoush ZAREYEE、Rezvaneh ASGHARI、Mohammad A. KHALILZADEH

  DOI：10.1016/s1872-2067(10)60300-2

  日期：2011.11

  Various alcohols and phenols were trimethylsilylated in excellent yields using hexamethyldisilazane in the presence of catalytic amounts of environmentally friendly, hydrophobic, highly thermal stable, and completely heterogeneous sulfonic acid functionalized mesostructured SBA-15 in dichloromethane at ambient temperature. Primary, bulky secondary, tertiary, and phenolic hydroxyl functional groups were transformed to the corresponding trimethylsilyl ethers in excellent yields. The simple experimental procedure was accompanied by easy recovery and the catalyst was reusable (at least 18 reaction cycles); these are attractive features of this protocol.
• One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to <i>gem</i>-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system
  作者：Roqayeh Khadem Moghaddam、Ghasem Aghapour

  DOI：10.1080/10426507.2020.1845680

  日期：2021.4.3

  Abstract A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides

  抽象的 首次描述了一种一锅法和氧化法，用于在中性介质中使用三氯异氰尿酸（TCCA）和三苯基膦（PPh 3）将苄基三甲基甲硅烷基（TMS）和四氢吡喃基（THP）醚转化为二氯化宝石。可以将包含吸电子或供电子基团的各种这些基材有效地转化成其相应的宝石-二氯化物，产率高至优异。本方法显示出高度的化学选择性，并且由于其一锅法性质符合绿色化学。