1-triphenylsilyloxy-3-phenylpropane | 634197-79-8

• 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-triphenylsilyloxy-3-phenylpropane
• 英文别名: Triphenyl(3-phenylpropoxy)silane；triphenyl(3-phenylpropoxy)silane
• CAS: 634197-79-8
• 化学式: C₂₇H₂₆OSi
• 分子量: 394.588
• InChiKey: LHSNOLLBIGRJQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-triphenylsilyloxy-3-phenyl-2-propene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以100%的产率得到1-triphenylsilyloxy-3-phenylpropane
  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

• Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation
  作者：Takashi Ikawa、Kazuyuki Hattori、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/j.tet.2004.05.098

  日期：2004.8

  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.