(S)-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman | 443903-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman
• 英文别名: (s)-(+)-2-(2-Acetoxyethyl)-6-benzyloxy-2,5,7,8-tetra-methylchroman；2-[(2S)-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl]ethyl acetate
• CAS: 443903-06-8
• 化学式: C₂₄H₃₀O₄
• 分子量: 382.5
• InChiKey: CKCVCAIYCFAOOA-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman 在 lithium hydroxide 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 49.0h， 生成 (S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol p-toluenesulfonate
  参考文献：
  名称：

  摘要：

  In the presence of lipase from the yeast Candida cylindracea, partial acetylation of (+/-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol with vinyl acetate gives S-(+)-acetate whose alkaline hydrolysis affords (S)-(-)-alcohol. Repeated enzymatic acetylation of the "residual" alcohol up to similar to39% conversion afforded the R-enantiomer. The enantiomeric alcohols were oxidized to (S)- or (R)-aldehydes having the same sign of \alpha\(D) as the original alcohols. These alcohols were converted into S-(+)- and R-(-)-enantiomers of the antioxidant MDL-73404, a hydrophilic analog of alpha-tocopherol.

  DOI：

  10.1023/a:1015001401902
• 作为产物：
  描述：

  乙酸乙烯酯 、 6-benzyloxy-2-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman 在 lipase from the yeast Candida cylindracea 作用下， 以 乙醚 为溶剂， 反应 10.0h， 生成 (S)-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol 、 (R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol 、 (S)-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman 、 (R)-(-)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman
  参考文献：
  名称：

  摘要：

  In the presence of lipase from the yeast Candida cylindracea, partial acetylation of (+/-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol with vinyl acetate gives S-(+)-acetate whose alkaline hydrolysis affords (S)-(-)-alcohol. Repeated enzymatic acetylation of the "residual" alcohol up to similar to39% conversion afforded the R-enantiomer. The enantiomeric alcohols were oxidized to (S)- or (R)-aldehydes having the same sign of \alpha\(D) as the original alcohols. These alcohols were converted into S-(+)- and R-(-)-enantiomers of the antioxidant MDL-73404, a hydrophilic analog of alpha-tocopherol.

  DOI：

  10.1023/a:1015001401902