1-(tert-butyldiphenylsilyl)oxy-3-phenyl-2-propene | 100009-32-3

• 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-(tert-butyldiphenylsilyl)oxy-3-phenyl-2-propene
• 英文别名: 1-tert-butyldiphenylsilyloxy-3-phenyl-2-propene；tert-butyl-diphenyl-[(E)-3-phenylprop-2-enoxy]silane
• CAS: 100009-32-3
• 化学式: C₂₅H₂₈OSi
• 分子量: 372.582
• InChiKey: BFSFPPMRLSSJCU-DTQAZKPQSA-N

物化性质

• 沸点：
  454.4±38.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-(tert-butyldiphenylsilyl)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 1-tert-butyldiphenylsilyloxy-3-phenylpropane
  参考文献：
  名称：

  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/

  摘要：

  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。

  DOI：

  10.1039/b211313a
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 3-苯基丙-2-烯-1-醇 在 硝酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以94%的产率得到1-(tert-butyldiphenylsilyl)oxy-3-phenyl-2-propene
  参考文献：
  名称：

  伯醇和仲醇快速叔丁基二苯基甲硅烷基化的温和方法

  摘要：

  开发了一种快速有效的方法来保护伯醇和仲醇的叔丁基二苯基甲硅烷基（tBDPS）醚。醇和tBDPSCl在DMF中与AgNO 3，NH 4 NO 3或NH 4 ClO 4的反应可提供相应甲硅烷基醚的良好收率

  DOI：

  10.1016/s0040-4039(00)79237-9

文献信息

• Deprotection of Acetals and Silyl Ethers Using a Polymer-Supported π-Acid Catalyst: Chemoselectivity and Polymer Effect
  作者：Nobuyuki Tanaka、Yukio Masaki

  DOI：10.1055/s-1999-3000

  日期：1999.12

  A polymeric dicyanoketene acetal (DCKA), prepared from a styrene monomer bearing dicyanoketene acetal functionality, was found to be an effective and recyclable catalyst in the chemoselective deprotection of acetals and silyl ethers. A remarkable acceleration accountable for the polymer effect was observed.

  一种由带有二氰基乙烯酮缩醛功能的苯乙烯单体制备的聚合型二氰基乙烯酮缩醛（DCKA），被发现是一种有效且可回收利用的催化剂，用于乙缩醛和硅醚的选择性脱保护反应。实验观察到由于聚合物效应引起的显著加速现象。
• Nonionic Superbase-Catalyzed Silylation of Alcohols
  作者：Bosco A. D'Sa、Dale McLeod、John G. Verkade

  DOI：10.1021/jo9701492

  日期：1997.7.1

  Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)(3)N, Ib, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 degrees C and on rare occasions in DMF from 24 to 80 degrees C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of Ib as a catalyst, tertiary alcohols were recovered unchanged.
• 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.
• LIU, HSING-JANG;HAN, IN-SUP, SYNTH. COMMUN., 1985, 15, N 9, 759-764
  作者：LIU, HSING-JANG、HAN, IN-SUP

  DOI：——

  日期：——