(Z)-(2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)ethenyloxy)trimethyl silane | 866416-81-1

• 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: (Z)-(2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)ethenyloxy)trimethyl silane
• 英文别名: [(Z)-2-benzhydryloxy-1-(2,5-dimethoxyphenyl)ethenoxy]-trimethylsilane
• CAS: 866416-81-1
• 化学式: C₂₆H₃₀O₄Si
• 分子量: 434.607
• InChiKey: OXMCHOQIGHNQMV-PLRJNAJWSA-N

物化性质

• 沸点：
  532.2±50.0 °C(predicted)
• 密度：
  1.074±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)ethenyloxy)trimethyl silane 在 4 A molecular sieve 、 trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine 吡啶 、 4-二甲氨基吡啶 、 双(三甲基硅基)过氧化物 、 O⁽⁹⁾-allyl-N-2',3',4'-trifluorobenzylhydrocinchonium*HF₂^(1-) 、 四氯化钛 、 四氯化锡 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 26.83h， 生成 2,5-dimethoxyphenyl 3-acetoxy-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric Glycolate Aldol Reactions Using Cinchonium Phase-Transfer Catalysts

  摘要：

  Cinchona phase-transfer catalysts (PTC) were developed for glycolate aldol reactions to give differentially protected 1,2-diol products. Silyl enol ether 9 reacted to generate benzhydryl-protected products. O-Allyl trifluorobenzyl cinchonium hydrofluoride CN-4 (20 mol %) catalyzed the addition of 9 to benzaldehyde to give 8 as a single syn-product in 76% yield and 80% ee. Recrystallization enriched the product to 95% ee, and a Baeyer-Villiger reaction transformed the product into useful ester intermediates.

  DOI：

  10.1021/ol051096a
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-benzhydryloxy-1-(2,5-dimethoxy-phenyl)-ethanone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以61%的产率得到(Z)-(2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)ethenyloxy)trimethyl silane
  参考文献：
  名称：

  Asymmetric Glycolate Aldol Reactions Using Cinchonium Phase-Transfer Catalysts

  摘要：

  Cinchona phase-transfer catalysts (PTC) were developed for glycolate aldol reactions to give differentially protected 1,2-diol products. Silyl enol ether 9 reacted to generate benzhydryl-protected products. O-Allyl trifluorobenzyl cinchonium hydrofluoride CN-4 (20 mol %) catalyzed the addition of 9 to benzaldehyde to give 8 as a single syn-product in 76% yield and 80% ee. Recrystallization enriched the product to 95% ee, and a Baeyer-Villiger reaction transformed the product into useful ester intermediates.

  DOI：

  10.1021/ol051096a

文献信息

• Asymmetric Glycolate Aldol Reactions Using Cinchonium Phase-Transfer Catalysts
  作者：Merritt B. Andrus、Jing Liu、Zhifeng Ye、John F. Cannon

  DOI：10.1021/ol051096a

  日期：2005.9.1

  Cinchona phase-transfer catalysts (PTC) were developed for glycolate aldol reactions to give differentially protected 1,2-diol products. Silyl enol ether 9 reacted to generate benzhydryl-protected products. O-Allyl trifluorobenzyl cinchonium hydrofluoride CN-4 (20 mol %) catalyzed the addition of 9 to benzaldehyde to give 8 as a single syn-product in 76% yield and 80% ee. Recrystallization enriched the product to 95% ee, and a Baeyer-Villiger reaction transformed the product into useful ester intermediates.