叔丁基(4-甲氧基苯氧基)二苯基硅烷 | 108534-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 叔丁基(4-甲氧基苯氧基)二苯基硅烷
• 英文名称: tert-butyl-4-methoxyphenoxydiphenylsilane
• 英文别名: 1-Diphenyl(tert-butyl)silyloxy-4-methoxybenzene；tert-butyl-(4-methoxyphenoxy)-diphenylsilane
• CAS: 108534-55-0
• 化学式: C₂₃H₂₆O₂Si
• 分子量: 362.544
• InChiKey: JHVKNSMCXUVYNN-UHFFFAOYSA-N

物化性质

• 熔点：
  69.5-71 °C
• 沸点：
  421.6±37.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 保留指数：
  2480

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  叔丁基(4-甲氧基苯氧基)二苯基硅烷 在 SO₃H silica gel 作用下， 反应 2.0h， 以91%的产率得到4-甲氧基苯酚
  参考文献：
  名称：

  Application of SO3H Silica Gel to Deprotection of Silyl Ethers

  摘要：

  A newly developed SO3H silica gel cleaved the O-Si bonds in various aryl and alkyl silyl ethers to give the corresponding phenols and alcohols in good to excellent yield. The crude filtrates contained no silyl residues. The solid phase Si-29 NMR analyses of the SO3H silica gel strongly suggested that the silyl residues were captured by silanol groups on the surface of the silica gel. The SO3H silica gel could be recycled at least ten times without any loss of activity. The disappearance of silyl residues in the crude filtrate was observed in even the 10th repetition. Our method provides an easily handled desilylation method that requires no further purification. Our method was also applicable to a selective desilylation reaction of a derivative 5 with different siloxy groups or desilylation of an alkaloid derivative 7.

  DOI：

  10.3987/com-12-12577
• 作为产物：
  描述：

  4-甲氧基苯酚 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以100%的产率得到叔丁基(4-甲氧基苯氧基)二苯基硅烷
  参考文献：
  名称：

  溶剂可及表面对无限稀释（29）Si和（13）C NMR的Hammett型依存关系的影响，该环溶解在氯仿和丙酮中的环取代甲硅烷基化苯酚。

  摘要：

  根据对位取代的O-甲硅烷基化苯酚，4-R-C6 H4 -O-SiR'2 R'的稀氯仿和丙酮溶液中的位移的浓度依赖性，可以确定无限稀释的（29）Si和（13）C NMR化学位移。 '（R = Me，MeO，H，F，Cl，NMe2，NH2和CF3），其中甲硅烷基部分包括不同大小的基团：二甲基甲硅烷基（R'= Me，R''= H），三甲基甲硅烷基（R' ＝ R″ ＝ Me），叔丁基二甲基甲硅烷基（R′＝ Me，R″ ＝ CMe3）和叔丁基二苯基甲硅烷基（R′＝ C6H5，R″ ＝ CMe3）。讨论了硅和C-1碳化学位移对Hammett取代基常数的依赖性。结果表明，这些化学位移的取代基敏感性通过与氯仿的结合而降低，

  DOI：

  10.1002/mrc.2860

文献信息

• Phase-Transfer Catalyzed <i>O</i>-Silyl Ether Deprotection Mediated by a Cyclopropenium Cation
  作者：Roya Mir、Travis Dudding

  DOI：10.1021/acs.joc.6b02733

  日期：2017.1.6

  The use of a cyclopropenium cation as a phase transfer catalyst for O-silyl ether deprotection is reported. Mechanistic insight into this deprotection methodology derived by linear free-energy relationships (LFER), quantum theory of atoms in molecules (QTAIM), and density functional theory (DFT) calculations are also provided.
• Mixed methyl-silyl ketals of quinones. Their preparation via anodic oxidation and their chemistry
  作者：Alan Stern、John S. Swenton

  DOI：10.1021/jo00389a023

  日期：1987.6
• STERN A.; SWENTON J. S., J. ORG. CHEM., 52,(1987) N 13, 2763-2768
  作者：STERN A.、 SWENTON J. S.

  DOI：——

  日期：——
• Application of SO3H Silica Gel to Deprotection of Silyl Ethers
  作者：Hiroshi Nagase、Hideaki Fujii、Takaaki Yamada、Miki Kuwada、Atom Hamasaki、Kazunori Nobuhara、Sumio Ozeki、Kohei Hayashida

  DOI：10.3987/com-12-12577

  日期：——

  A newly developed SO3H silica gel cleaved the O-Si bonds in various aryl and alkyl silyl ethers to give the corresponding phenols and alcohols in good to excellent yield. The crude filtrates contained no silyl residues. The solid phase Si-29 NMR analyses of the SO3H silica gel strongly suggested that the silyl residues were captured by silanol groups on the surface of the silica gel. The SO3H silica gel could be recycled at least ten times without any loss of activity. The disappearance of silyl residues in the crude filtrate was observed in even the 10th repetition. Our method provides an easily handled desilylation method that requires no further purification. Our method was also applicable to a selective desilylation reaction of a derivative 5 with different siloxy groups or desilylation of an alkaloid derivative 7.
• The effect of solvent accessible surface on Hammett-type dependencies of infinite dilution 29Si and 13C NMR shifts in ring substituted silylated phenols dissolved in chloroform and acetone
  作者：Vratislav Blechta、Stanislav Šabata、Jan Sýkora、Jiří Hetflejš、Ludmila Soukupová、Jan Schraml

  DOI：10.1002/mrc.2860

  日期：2012.2

  Infinite dilution (29)Si and (13)C NMR chemical shifts were determined from concentration dependencies of the shifts in dilute chloroform and acetone solutions of para substituted O-silylated phenols, 4-R-C6 H4 -O-SiR'2 R'' (R = Me, MeO, H, F, Cl, NMe2, NH2, and CF3), where the silyl part included groups of different sizes: dimethylsilyl (R' = Me, R'' = H), trimethylsilyl (R' = R'' = Me), tert-butyldimethylsilyl

  根据对位取代的O-甲硅烷基化苯酚，4-R-C6 H4 -O-SiR'2 R'的稀氯仿和丙酮溶液中的位移的浓度依赖性，可以确定无限稀释的（29）Si和（13）C NMR化学位移。 '（R = Me，MeO，H，F，Cl，NMe2，NH2和CF3），其中甲硅烷基部分包括不同大小的基团：二甲基甲硅烷基（R'= Me，R''= H），三甲基甲硅烷基（R' ＝ R″ ＝ Me），叔丁基二甲基甲硅烷基（R′＝ Me，R″ ＝ CMe3）和叔丁基二苯基甲硅烷基（R′＝ C6H5，R″ ＝ CMe3）。讨论了硅和C-1碳化学位移对Hammett取代基常数的依赖性。结果表明，这些化学位移的取代基敏感性通过与氯仿的结合而降低，