2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)-3-(furan-3-yl)-3-hydroxypropan-1-one

• 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: 2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)-3-(furan-3-yl)-3-hydroxypropan-1-one
• 英文别名: (2S,3R)-2-benzhydryloxy-1-(2,5-dimethoxyphenyl)-3-(furan-3-yl)-3-hydroxypropan-1-one
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: WGGWLWHABWVYRW-NAKRPHOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-benzhydryloxy-1-(2,5-dimethoxy-phenyl)-ethanone 在 O⁽⁹⁾-allyl-N-2',3',4'-trifluorobenzylhydrocinchonium*HF₂^(1-) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 2-(benzhydryloxy)-1-(2,5-dimethoxyphenyl)-3-(furan-3-yl)-3-hydroxypropan-1-one
  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.