tert-butyl(4-(tert-butyldimethylsilyloxy)-3-methoxybenzyloxy)dimethylsilane | 139140-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl(4-(tert-butyldimethylsilyloxy)-3-methoxybenzyloxy)dimethylsilane
• 英文别名: Vanillyl alcohol, 2TBDMS derivative；tert-butyl-[[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]methoxy]-dimethylsilane
• CAS: 139140-12-8
• 化学式: C₂₀H₃₈O₃Si₂
• 分子量: 382.691
• InChiKey: UOKVEZAOLUVBIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl(4-(tert-butyldimethylsilyloxy)-3-methoxybenzyloxy)dimethylsilane 在 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以92%的产率得到4-((tert-butyldimethylsilyloxy)methyl)-2-methoxyphenol
  参考文献：
  名称：

  烷基或芳基甲硅烷基醚从芳基，烷基双甲硅烷基醚中选择性脱保护

  摘要：

  开发了一对互补方法，分别使用CeCl 3 ·7H 2 O / CH 3 CN和LiOH / DMF从相应的双甲硅烷基醚中选择性脱保护烷基和芳基甲硅烷基醚，且收率很高。

  DOI：

  10.1016/s0040-4039(02)00942-5
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 tert-butyl(4-(tert-butyldimethylsilyloxy)-3-methoxybenzyloxy)dimethylsilane
  参考文献：
  名称：

  Lee, Adam Shih-Yuan; Yeh, Hsiu-Chih; Yeh, Ming-Kuo, Journal of the Chinese Chemical Society, 1995, vol. 42, # 6, p. 919 - 922

  摘要：

  DOI：

文献信息

• A mild, efficient, and selective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using dicationic ionic liquid as a catalyst
  作者：Arvind H. Jadhav、Hern Kim

  DOI：10.1016/j.tetlet.2012.07.108

  日期：2012.9

  Selective deprotection of alkyl TBDMS ether in the presence of phenolic TBDMS ether using dicationic ionic liquid [tetraEG(mim)2][OMs]2 as a homogeneous catalyst showed significant catalytic activity in methanol at ambient temperature to produce respective alcohol in excellent yield. The present environmentally benign catalytic system is found to be very convenient, fast, high yielding, and clean method

  使用阳离子性离子液体[tetraEG（mim）2 ] [OMs] 2作为均相催化剂，在酚类TBDMS醚存在下对烷基TBDMS醚进行选择性脱保护，在甲醇中，在环境温度下显示出显着的催化活性，从而以优异的收率生产了相应的醇。发现即使在存在其他敏感的有机官能团例如醛，甲氧基和乙酸酯的情况下，本发明对环境无害的催化体系也非常方便，快速，高收率和清洁的用于烷基甲硅烷基醚的选择性脱甲硅烷基化的方法。
• Aryl, Alkyl<i>bis</i>-SilylEthers: Rapid Access to Monoprotected Aryl Alkyl and Biaryl Ethers
  作者：Gabriel Fenteany、Sudha V. Ankala

  DOI：10.1055/s-2003-38744

  日期：——

  A simple one-pot procedure has been developed for the selective etherification of aryl silyl ethers in aryl, alkyl bis-silyl ethers to generate alkyl tert-butyldimethylsilyl-protected aryl alkyl ethers and biaryl ethers in good to excellent yields.

  已经开发了一种简单的一锅法，用于选择性醚化芳香族硅醚与芳香族、烷基双硅醚，从而生成烷基叔丁基二甲基硅基保护的芳香烷醚和联芳醚，产率良好至优异。
• A mild and efficient method for the selective cleavage of tert-butyldimethylsilyl ethers to alcohols
  作者：Gourhari Maiti、Subhas Chandra Roy

  DOI：10.1016/s0040-4039(96)02353-2

  日期：1997.1

  A mild and efficient method for the selective deprotection of primary allylic and homoallylic, primary benzylic and aryl tert-butyldimethylsilyl (TBDMS) ethers has been established using a combination of H2O and DMSO at 90 degrees C. All other primary and secondary TBDMS ethers remained unaffected under the reaction condition. The method is very effective in deprotection of TBDMS ethers in the presence of other sensitive functional groups. Copyright (C) 1996 Published by Elsevier Science Ltd
• An efficient and chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using tailor-made ionic liquid
  作者：Vinod H. Jadhav、Sang Bong Lee、Hwan-Jeong Jeong、Seok Tae Lim、Myung-Hee Sohn、Dong Wook Kim

  DOI：10.1016/j.tetlet.2012.02.016

  日期：2012.4

  Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using tailor-made ionic liquid [dihexaEGim][OMs] (dihexaEGim = dihexaethylene glycolic imidazolium salt) as an organic catalyst with alkali-metal fluoride in tert-amyl alcohol. On the contrary, all TBDMS protecting groups can be cleaved cleanly from the bis-TBDMS ether using the same reaction in CH3CN solvent instead of tert-alcohol at 100 degrees C. This [dihexaEGim][OMs]/tert-amyl alcohol media system allows the highly selective phenolic deprotection reaction of various bis-TBDMS ethers containing both phenolic and aliphatic TBDMS ethers to provide the corresponding phenols in high yield. (C) 2012 Elsevier Ltd. All rights reserved.
• A simple and highly chemoselective desilylation of tert-butyldimethylsilyl ethers
  作者：Adam Shih-Yuan Lee、Hsiu-Chih Yeh、Ming-Hung Tsai

  DOI：10.1016/0040-4039(95)01423-f

  日期：1995.9

  The use of a 0.25M CH3OH/CCl4 (1:1) solvent mixture under ultrasound for the selective deprotection of tert-butyldimethlysilyl ethers of benzyl alcohols is described. This method enables to deprotect tert-butyldimethlysilyl ethers of primary alcohols, whereas tert-butyldimethlysilyl ethers of secondary and tertiary alcohols were stable under the reaction condition.