6-benzyloxy-2-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman | 53713-43-2

• 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: 6-benzyloxy-2-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman
• 英文别名: 2-[(+/-)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol；2-(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethanol；2-(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-yl)-ethanol；2-(6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethanol；(+/-)-6-benzyloxy-2-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman；rac.-2-(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)-ethanol；2-(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl)ethanol
• CAS: 53713-43-2
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: FEZFOZDYAFUPAO-UHFFFAOYSA-N

物化性质

• 沸点：
  485.5±45.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

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：

  6-benzyloxy-2-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 (+/-)-{2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}trimethylammonium 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：

  三甲基氢醌 在 三氯化铝 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.25h， 生成 6-benzyloxy-2-(2-hydroxyethyl)-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

文献信息

• Antioxidant chroman compounds
  申请人：Hoffman-La Roche Inc.

  公开号：US03947473A1

  公开（公告）日：1976-03-30

  The (6-hydroxy-chroman-2-yl) acetic or carboxylic acid derivatives useful as antioxidants and a method for preparing these derivatives from hydroquinones and intermediates in this synthesis as well as the use of these derivatives as intermediates in the preparation of optically active alpha-tocopherol.

  (6-羟基-色苷-2-基) 乙酸或羧酸衍生物可用作抗氧化剂，以及从对苯二酚和合成中间体制备这些衍生物的方法，以及在制备光学活性α-生育酚中使用这些衍生物作为中间体。
• Synthesis of vitamin E
  申请人：Hoffman-La Roche Inc.

  公开号：US04151205A1

  公开（公告）日：1979-04-24

  A synthesis of vitamin E in racemic or optically active forms from methacryolein or beta-hydroxyisobutyric acid including intermediates in this synthesis.

  从甲基丙烯醛或β-羟基异丁酸中合成光学活性或外消旋形式的维生素E，包括在这个合成中的中间体。
• Protected alcohols
  申请人：Hoffmann-La Roche Inc.

  公开号：US04191842A1

  公开（公告）日：1980-03-04

  A synthesis of vitamin E in racemic or optically active forms from methacryolein or beta-hydroxyisobutyric acid including intermediates in this synthesis.

  从甲基丙烯酰或β-羟基异丁酸中合成光学活性或外消旋形式的维生素E，包括在此合成过程中的中间体。
• Intermediates in the synthesis of vitamin E
  申请人：Hoffmann-La Roche Inc.

  公开号：US04051153A1

  公开（公告）日：1977-09-27

  A synthesis of vitamin E in racemic or optically active forms from methacryolein or beta-hydroxyisobutyric acid including intermediates in this synthesis.

  从甲基丙烯酰基或β-羟基异丁酸合成光学活性或外消旋形式的维生素E，包括在合成过程中的中间体。
• Thiazolidine derivatives, their preparation and compositions containing
  申请人：Sankyo Company Limited

  公开号：US04572912A1

  公开（公告）日：1986-02-25

  The compounds of formula (I): ##STR1## [in which: R.sup.1 and R.sup.2 are the same or different and each represents hydrogen or C.sub.1 -C.sub.5 alkyl; R.sup.3 represents hydrogen, an acyl group, a (C.sub.1 -C.sub.6 alkoxy)carbonyl group or an aralkyloxycarbonyl group; R.sup.4 and R.sup.5 are the same or different and each represents hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, or R.sup.4 and R.sup.5 together represent a C.sub.1 14 C.sub.4 alkylenedioxy group; n is 1, 2 or 3; W represents the --CH.sub.2 --, >CO or >CH--OR.sup.6 group (in which R.sup.6 represents any one of the atoms or groups defined for R.sup.3 and may be the same as or different from R.sup.3); and Y and Z are the same or different and each represents oxygen or imino] and pharmaceutically acceptable salts thereof have various valuable therapeutic effects on the blood system and may be prepared by a process which includes reacting a corresponding halopropionic acid derivative with thiourea.

  式(I)的化合物：##STR1## [其中：R.sup.1和R.sup.2相同或不同，分别代表氢或C.sub.1-C.sub.5烷基；R.sup.3代表氢，酰基，(C.sub.1-C.sub.6烷氧基)羰基或苯基甲氧基羰基；R.sup.4和R.sup.5相同或不同，分别代表氢，C.sub.1-C.sub.5烷基或C.sub.1-C.sub.5烷氧基，或R.sup.4和R.sup.5一起代表C.sub.1-C.sub.4烷二氧基基团；n为1、2或3；W代表--CH.sub.2 --、>CO或>CH--OR.sup.6基团（其中R.sup.6代表R.sup.3定义的任意一个原子或基团，并且可能与R.sup.3相同或不同）；Y和Z相同或不同，分别代表氧或亚胺基]及其药学上可接受的盐在血液系统上具有各种有价值的治疗效果，并可通过将相应的卤代丙酸衍生物与硫脲反应制备。

表征谱图