(R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol | 79434-91-6

• 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: (R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol
• 英文别名: (+)-(R)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol；(r)-2-[6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol；2-[(2R)-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl]ethanol
• CAS: 79434-91-6
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: FEZFOZDYAFUPAO-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87.5%的产率得到(R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]acetaldehyde
  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：

  (R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]acetaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以90%的产率得到(R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol
  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

文献信息

• US4051153A
  申请人：——

  公开号：US4051153A

  公开（公告）日：1977-09-27
• US4151205A
  申请人：——

  公开号：US4151205A

  公开（公告）日：1979-04-24
• US4191842A
  申请人：——

  公开号：US4191842A

  公开（公告）日：1980-03-04
• ——
  作者：V. N. Odinokov、A. Yu. Spivak、G. A. Emel"yanova、G. D. Gamalevich、E. P. Serebryakov

  DOI：10.1023/a:1015001401902

  日期：——

  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.