1-(triisopropylsilyl)oxy-3-phenyl-2-propene | 423171-96-4

• 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-(triisopropylsilyl)oxy-3-phenyl-2-propene
• 英文别名: [(E)-3-phenylprop-2-enoxy]-tri(propan-2-yl)silane
• CAS: 423171-96-4
• 化学式: C₁₈H₃₀OSi
• 分子量: 290.521
• InChiKey: LYESRAAEFRQPJM-JLHYYAGUSA-N

物化性质

• 沸点：
  349.3±21.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-(triisopropylsilyl)oxy-3-phenyl-2-propene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3-苯丙醇
  参考文献：
  名称：

  Unexpected deprotection of silyl and THP ethers induced by serious disparity in the quality of Pd/C catalysts and elucidation of the mechanism

  摘要：

  Commercial Pd/C catalysts show different catalytic activity toward the deprotection of silyl and THP ethers. The Pd/C purchased from Merck and ACROS exhibits marked tendency to cleave these protective groups unexpectedly without hydrogen conditions although Aldrich's Pd/C (20,569-9) is inactive in the absence of hydrogen. It was proved that the Pd/C disparity toward the deprotection of TES and THP ethers results from residual acids and/or palladium chloride in the production process of Pd/Cs. Although a TES ether cleavage reaction in the absence of hydrogen and a THP ether cleavage reaction in the presence of hydrogen using 10% Pd/C were recently published, we could conclude they were only an acid-catalyzed solvolysis, the acid being released from the catalyst. Hydrogen is essential for the actual 10% Pd/C-catalyzed cleavage of TES ethers and THP ethers which must be stable under the true Pd/C-catalyzed hydrogenation conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.040
• 作为产物：
  描述：

  三异丙基氯硅烷 、 3-苯基丙-2-烯-1-醇 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以77%的产率得到1-(triisopropylsilyl)oxy-3-phenyl-2-propene
  参考文献：
  名称：

  使用硼甲基锌卡宾对烯丙醚进行非对映选择性硼环丙烷化

  摘要：

  描述了 (E)-和 (Z)-烯丙基醚和苯乙烯衍生物通过 Simmons-Smith 反应使用新型硼甲基锌卡宾进行硼环丙烷化。卡宾前体是通过 3 步序列从廉价且市售的起始材料制备的。这种方法允许以高产率和非对映选择性制备 1,2,3-取代的硼环丙烷。还进行了几个后功能化反应来说明这些构建块的多功能性。

  DOI：

  10.1021/jacs.6b09090

文献信息

• A remarkable solvent effect toward the Pd/C-catalyzed cleavage of silyl ethersElectronic supplementary information (ESI) available: characterization data and references and supplementary Tables 4 and 5. See http://www.rsc.org/suppdata/cc/b2/b211313a/
  作者：Hironao Sajiki、Takashi Ikawa、Kazuyuki Hattori、Kosaku Hirota

  DOI：10.1039/b211313a

  日期：2003.2.20

  Selective hydrogenation conditions of olefin, benzyl ether and acetylene functionalities in the presence of TBDMS or TES ether have been developed.

  已经开发出在TBDMS或TES醚存在下，对烯烃、苄醚和炔烃功能团进行选择性加氢的条件。
• 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.
• Iridium-Catalyzed Enantioselective Synthesis of Allylic Alcohols: Silanolates as Hydroxide Equivalents
  作者：Isabelle Lyothier、Christian Defieber、Erick M. Carreira

  DOI：10.1002/anie.200602408

  日期：2006.9.18
• Diastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid
  作者：Guillaume Benoit、André B. Charette

  DOI：10.1021/jacs.6b09090

  日期：2017.2.1

  borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities

  描述了 (E)-和 (Z)-烯丙基醚和苯乙烯衍生物通过 Simmons-Smith 反应使用新型硼甲基锌卡宾进行硼环丙烷化。卡宾前体是通过 3 步序列从廉价且市售的起始材料制备的。这种方法允许以高产率和非对映选择性制备 1,2,3-取代的硼环丙烷。还进行了几个后功能化反应来说明这些构建块的多功能性。
• Unexpected deprotection of silyl and THP ethers induced by serious disparity in the quality of Pd/C catalysts and elucidation of the mechanism
  作者：Takashi Ikawa、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/j.tet.2004.05.040

  日期：2004.7

  Commercial Pd/C catalysts show different catalytic activity toward the deprotection of silyl and THP ethers. The Pd/C purchased from Merck and ACROS exhibits marked tendency to cleave these protective groups unexpectedly without hydrogen conditions although Aldrich's Pd/C (20,569-9) is inactive in the absence of hydrogen. It was proved that the Pd/C disparity toward the deprotection of TES and THP ethers results from residual acids and/or palladium chloride in the production process of Pd/Cs. Although a TES ether cleavage reaction in the absence of hydrogen and a THP ether cleavage reaction in the presence of hydrogen using 10% Pd/C were recently published, we could conclude they were only an acid-catalyzed solvolysis, the acid being released from the catalyst. Hydrogen is essential for the actual 10% Pd/C-catalyzed cleavage of TES ethers and THP ethers which must be stable under the true Pd/C-catalyzed hydrogenation conditions. (C) 2004 Elsevier Ltd. All rights reserved.