Trimethyl-[1-(4-phenylmethoxyphenyl)ethenoxy]silane | 247135-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Trimethyl-[1-(4-phenylmethoxyphenyl)ethenoxy]silane
• CAS: 247135-72-4
• 化学式: C₁₈H₂₂O₂Si
• 分子量: 298.457
• InChiKey: GXWDGTSHWHTOHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• 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：

  Trimethyl-[1-(4-phenylmethoxyphenyl)ethenoxy]silane 在 Selectfluor 作用下， 生成 1-(4-(benzyloxy)phenyl)-2-fluoroethanone
  参考文献：
  名称：

  Ruthenium-catalysed asymmetric transfer hydrogenation of para-substituted α-fluoroacetophenones

  摘要：

  The first examples of asymmetric transfer hydrogenation of alpha-fluoroacetophenones are reported. Eight para-substituted a-fluoroacetophenones have been reduced using four catalytic systems constructed of [RuCl2(p-cymene)(2)](2) or [RuCl2(mesitylene)(2)](2) in combinations with each of the ligands (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine ((R,R)-TsDPEN) and (1R,2R)-N-(p-toluenesulfonyl)-1,2cyclohexanediamine ((R,R)-TsCYDN). All reactions were performed in both water and formic acid/triethylamine. The highest enantioselectivity was obtained using the (R,R)-TsDPEN ligand in a formic acid/triethylamine mixture, giving the (S)-1-aryl-2-fluoroethanols in high to moderate enantiomeric excess (97.5-84.5%). For this solvent system the presence of electron withdrawing groups in the para position reduced the enantioselectivity. Reactions performed in water generally gave lower enantioselectivity and reaction rate, although RuCl(mesitylene)-(R,R)-TsDPEN yielded the product alcohols with enantiomeric excess in the range of 95.5-76.5%. (c) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.03.011
• 作为产物：
  描述：

  三甲基氯硅烷 、 4-苯甲氧基苯乙酮 在 lithium hexamethyldisilazane 作用下， 生成 Trimethyl-[1-(4-phenylmethoxyphenyl)ethenoxy]silane
  参考文献：
  名称：

  Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones

  摘要：

  para-Substituted alpha-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F-TEDA-BF4, 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[ 2.2.2]octane bis-(tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F-TEDA-BF4 mediated fluorination of acetophenones in methanol resulted in a mixture of alpha-fluoroacetophenones and the corresponding 2-fluoro- 1,1 -dimethyl acetals. The dimethyl acetals were hydrolysed using trifluoroacetic acid in water to maximise the yield of the product. Nucleophilic fluorination of alpha-bromoacetophenones using tetrabutylammoniurn hydrogen bifluoride (TBABF) led to moderate yield when having electron-donating substituents, whereas low yields were experienced when more electron-withdrawing substituents were introduced. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.060