4-Trimethyl-silyl-phenyl-methyl-carbinol | 17993-99-6

• 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: 4-Trimethyl-silyl-phenyl-methyl-carbinol
• 英文别名: a-Methyl-p-(trimethylsilyl)benzyl alcohol；1-(4-trimethylsilylphenyl)ethanol
• CAS: 17993-99-6
• 化学式: C₁₁H₁₈OSi
• 分子量: 194.349
• InChiKey: OXDHNJKICPOXOH-UHFFFAOYSA-N

物化性质

• 熔点：
  46-47 °C
• 沸点：
  91-92 °C(Press: 2 Torr)
• 密度：
  0.9611 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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-methyl-carbinol 在 N-碘代丁二酰亚胺 、 六氟异丙醇 、 sodium acetate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 iodometomidate
  参考文献：
  名称：

  使用有机硅烷和有机锗烷作为放射性标记前体的碱介导的芳烃放射性碘化

  摘要：

  弱碱介导过程的发现允许从硅烷或锗烷发生放射性碘化。结果的比较表明，芳基锗烷具有作为放射性碘化前体的临床潜力。通过[ 125 I]IMTO和[ 125 I]MIBG的标记证明了概念证明，从而提供了使用无毒前体的放射性碘去锡工艺的替代方法。

  DOI：

  10.1002/chem.202203366
• 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-methyl-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

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 27, page 82 - 85
  作者：

  DOI：——

  日期：——
• 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.
• Bazant; Matousek, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 3758,3761
  作者：Bazant、Matousek

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  日期：——
• Petrow et al., Doklady Akademii Nauk SSSR, 1958, vol. 118, p. 957
  作者：Petrow et al.

  DOI：——

  日期：——
• Kohama, Nippon Kagaku Zasshi, 1959, vol. 80, p. 284
  作者：Kohama

  DOI：——

  日期：——