1-triethylsilyloxy-2-(2-propenyl)benzene | 134249-16-4

• 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: 1-triethylsilyloxy-2-(2-propenyl)benzene
• 英文别名: Triethyl-(2-prop-2-enylphenoxy)silane
• CAS: 134249-16-4
• 化学式: C₁₅H₂₄OSi
• 分子量: 248.44
• InChiKey: RHQIVIGADXPTRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  286.2±19.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-triethylsilyloxy-2-(2-propenyl)benzene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以83%的产率得到2-正丙基苯酚
  参考文献：
  名称：

  Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

  摘要：

  Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.098
• 作为产物：
  描述：

  三乙基氯硅烷 、 2-烯丙基酚 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到1-triethylsilyloxy-2-(2-propenyl)benzene
  参考文献：
  名称：

  Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

  摘要：

  Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.098

文献信息

• Reduction of Olefins Using Ruthenium Carbene Catalysts and Silanes
  作者：Peter I. Dalko、Janine Cossy、Candice Menozzi

  DOI：10.1055/s-2005-872695

  日期：——

  Ruthenium carbene complexes are able to mediate reduction of olefins in the presence of trialkylsilanes. Under these reduction conditions, when kinetically favorable ring-closing metathesis is possible, a one-pot cyclization-reduction sequence can be performed.

  在三烷基硅烷的存在下，钌卡宾配合物能够介导烯烃的还原。在这些还原条件下，当动力学有利的闭环复分解是可能的时，可以进行一锅环化还原序列。