4-Trimethyl-silyl-phenyl-aethyl-carbinol | 18052-25-0

• 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: 4-Trimethyl-silyl-phenyl-aethyl-carbinol
• 英文别名: a-Ethyl-p-(trimethylsilyl)benzyl alcohol；1-(4-trimethylsilylphenyl)propan-1-ol
• CAS: 18052-25-0
• 化学式: C₁₂H₂₀OSi
• 分子量: 208.376
• InChiKey: XLOLWPUAZUBKNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-Trimethyl-silyl-phenyl-aethyl-carbinol 在 rac-ethanediyl-bis(1-indenyl)zirconium dichloride 、 Isobutylmagnesium chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 生成 5-(4-(trimethylsilyl)phenyl)heptan-1-ol
  参考文献：
  名称：

  光致低价锆催化醚交叉电偶联

  摘要：

  利用光诱导二茂锆催化实现醚的还原偶联，具有显着的活性和交叉选择性。机理研究表明，低价二茂锆的光激发促进了苄基C( sp3 )−O键的断裂，产生与Zr中心重组的苄基自由基。随后的碳镁化生成苄基格氏试剂，用于下游与脂肪族醚的偶联。

  DOI：

  10.1002/anie.202405449
• 作为产物：
  描述：

  对溴苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 4-Trimethyl-silyl-phenyl-aethyl-carbinol
  参考文献：
  名称：

  Highly enantioselective dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipoprotein lipase preparation

  摘要：

  The kinetic and dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipase preparation containing lipoprotein lipase, dextrin, and ionic surfactant 1 has been explored. It was found that all the trimethylsilyl-containing substrates were accepted by lipoprotein lipase-dextrin 1 (LPL-D1) with perfect enantioselectivity (E = >200). As a result, the dynamic kinetic resolution of these substrates with LPL-D1 in the presence of a Ru-based racemization catalyst provided single enantiomeric products (>99% ee) with good yields. Furthermore, the dynamic kinetic resolution products were readily desilylated or halodesilylated to yield enantiopure alkyl aryl carbinols. Thus a useful protocol for the highly enantioselective synthesis of alkyl aryl carbinols, particularly those carrying a long alkyl chain (C-6-C-10) has been established. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.010

文献信息

• Application of a promiscuous Arthrobacter sp. from Antarctic in aerobic (R)-selective deracemization and anaerobic (S)-selective reduction
  作者：Dayvson J. Palmeira、Lidiane S. Araújo、Juliana C. Abreu、Leandro H. Andrade

  DOI：10.1016/j.molcatb.2014.09.016

  日期：2014.12

  Inspired by enzyme-catalyzed reactions with microorganisms found in harsh marine environments, in which the amount of oxygen is restrict, we have shown that Arthrobacter sp. can perform different chemical transformations by switching from anaerobic to aerobic reaction conditions. Depending on the presence or absence of oxygen, either alcohol deracemization or ketone reduction with enantiocomplementary selectivities can be performed by the same microorganism. For example, reactions performed in the presence of oxygen favored the deracemization process, in which a racemic mixture of 1-(4-methylphenyl) ethanol was enriched to the (R)-alcohol in high conversion (94%) and high enantiomeric excess (94%). On the other hand, reaction in the absence of oxygen favored the reduction process, in which 4-methyl-acetophenone was converted to the (S)-alcohol in good conversion (58%) and excellent enantiomeric excess (> 99%). These concepts were applied for both deracemization and enantio selective reduction of heteroatom-containing (silicon, phosphorus, tin and boron) molecules. Moreover, preparative scale reactions were also performed for both chemical processes. (C) 2014 Elsevier B.V. All rights reserved.