(2R)-(+)-2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol | 94353-05-6

• 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: (2R)-(+)-2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol
• 英文别名: (R)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-bromoethyl)-chroman；(2R)-2-(2-bromoethyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol
• CAS: 94353-05-6
• 化学式: C₁₅H₂₁BrO₂
• 分子量: 313.235
• InChiKey: ODWFNKAXBDDVMD-OAHLLOKOSA-N

物化性质

• 沸点：
  419.2±45.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-(+)-2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2R)-(+)-<2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethyl>dimethylsulfonium 4-methylbenzenesulfonate
  参考文献：
  名称：

  Cardioselective Ammonium, Phosphonium, and Sulfonium Analogs of .alpha.-Tocopherol and Ascorbic Acid That Inhibit in Vitro and ex Vivo Lipid Peroxidation and Scavenge Superoxide Radicals

  摘要：

  Analogues of alpha-tocopherol and ascorbic acid with permanently cationic substituents, i.e., phosphonium (8, 9), sulfonium (11), acylhydrazinium (13, 14), and ammonium (1, 16, 21), were synthesized, and the 2R and 2S enantiomers of the alpha-tocopherol analogues 1, 8, 11, and 13 were separated. The compounds were found to scavenge lipoperoxyl and superoxide radicals in vitro and accumulate in heart tissue (cardioselectivity) as demonstrated by measurement of ex vivo inhibition of lipid peroxidation in mouse heart homogenates and confirmed by HPLC determination of drug concentrations for 1 and 11. The 2R and 2S enantiomers of 1 inhibited ex vivo lipid peroxidation to an equal extent. Thus the in vivo uptake into myocytes (cardioselectivity) is independent of the geometry at the chiral center and common to permanently cationic compounds.

  DOI：

  10.1021/jm00015a010
• 作为产物：
  描述：

  (R)-2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethanol 生成 (2R)-(+)-2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol
  参考文献：
  名称：

  Novel optically active chroman derivatives, their preparation and novel

  摘要：

  利用一种方法制备一种具有一般式Ia和Ib的新型光学活性的色滤衍生物##STR1##其中R.sup.1、R.sup.2、R.sup.3和R.sup.4分别为氢或烷基，X为--OH、--O--CO-烷基、--O-烷基、--O-对甲苯磺酰基、--O-甲烷磺酰基、--O-苯甲磺酰基、Cl、Br或I，所述方法包括(a)将一般式I'的消旋体##STR2##在侧链中与羧酸酯化，然后与一般式III的光学活性羧酸卤化物##STR3##或相应的羧酸酐酰化，得到色滤衍生物IV##STR4##或(b)将消旋体I'在侧链中与III来源的羧酸酯化，如有必要，将得到的酯与羧酸卤化物酰化以得到IV'##STR5##所得的混合物IV或IV'，由两个对映异构体组成，通过分馏结晶进行分离，将对映异构体水解为醇Ia和Ib，如有需要，这些醇可以以常规方式转化为其他化合物Ia和Ib。还声明了有用的光学活性色滤衍生物Ia和Ib以及对映异构的色滤酰基酯IV和IV'。

  公开号：

  US04645845A1

文献信息

• Novel optically active chroman derivatives, their preparation and novel
  申请人：BASF Aktiengesellschaft

  公开号：US04645845A1

  公开（公告）日：1987-02-24

  Novel optically active chroman derivatives of the general formulae Ia and Ib ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or alkyl and X is --OH, --O--CO-alkyl, --O-alkyl, --O-tosyl, --O-mesyl, --O-benzenesulfonyl, Cl, Br or I, are prepared by a process in which (a) the racemate of the formula I' ##STR2## is esterified in the side chain with a carboxylic acid and then acylated with an optically active carboxylic acid halide of the general formula III ##STR3## or with the corresponding carboxylic anhydride, to give a chroman derivative IV ##STR4## or (b) the racemate I' is esterified in the side chain with the carboxylic acid from which III is derived, and, if required, the resulting ester is acylated with a carboxylic acid halide to give IV' ##STR5## the resulting mixture IV or IV', which consists of two diastereomers, is resolved by fractional crystallization, the diastereomers are hydrolyzed to the alcohols Ia and Ib and, if desired, these are converted to the other compounds Ia and Ib in a conventional manner. Useful optically active chroman derivatives Ia and Ib and diastereomeric chromanyl esters IV and IV' are also claimed.

  利用一种方法制备一种具有一般式Ia和Ib的新型光学活性的色滤衍生物##STR1##其中R.sup.1、R.sup.2、R.sup.3和R.sup.4分别为氢或烷基，X为--OH、--O--CO-烷基、--O-烷基、--O-对甲苯磺酰基、--O-甲烷磺酰基、--O-苯甲磺酰基、Cl、Br或I，所述方法包括(a)将一般式I'的消旋体##STR2##在侧链中与羧酸酯化，然后与一般式III的光学活性羧酸卤化物##STR3##或相应的羧酸酐酰化，得到色滤衍生物IV##STR4##或(b)将消旋体I'在侧链中与III来源的羧酸酯化，如有必要，将得到的酯与羧酸卤化物酰化以得到IV'##STR5##所得的混合物IV或IV'，由两个对映异构体组成，通过分馏结晶进行分离，将对映异构体水解为醇Ia和Ib，如有需要，这些醇可以以常规方式转化为其他化合物Ia和Ib。还声明了有用的光学活性色滤衍生物Ia和Ib以及对映异构的色滤酰基酯IV和IV'。
• GRISAR, J. MARTIN;PETTY, MARGARET;BOLKENIUS, FRANK
  作者：GRISAR, J. MARTIN、PETTY, MARGARET、BOLKENIUS, FRANK

  DOI：——

  日期：——
• Neue optisch aktive Chromanderivate, Verfahren zu deren Herstellung sowie neue Zwischenprodukte
  申请人：BASF Aktiengesellschaft

  公开号：EP0122426B1

  公开（公告）日：1988-01-27
• US4645845A
  申请人：——

  公开号：US4645845A

  公开（公告）日：1987-02-24
• Cardioselective Ammonium, Phosphonium, and Sulfonium Analogs of .alpha.-Tocopherol and Ascorbic Acid That Inhibit in Vitro and ex Vivo Lipid Peroxidation and Scavenge Superoxide Radicals
  作者：J. Martin Grisar、Gilbert Marciniak、Frank N. Bolkenius、Joelle Verne-Mismer、Eugene R. Wagner

  DOI：10.1021/jm00015a010

  日期：1995.7

  Analogues of alpha-tocopherol and ascorbic acid with permanently cationic substituents, i.e., phosphonium (8, 9), sulfonium (11), acylhydrazinium (13, 14), and ammonium (1, 16, 21), were synthesized, and the 2R and 2S enantiomers of the alpha-tocopherol analogues 1, 8, 11, and 13 were separated. The compounds were found to scavenge lipoperoxyl and superoxide radicals in vitro and accumulate in heart tissue (cardioselectivity) as demonstrated by measurement of ex vivo inhibition of lipid peroxidation in mouse heart homogenates and confirmed by HPLC determination of drug concentrations for 1 and 11. The 2R and 2S enantiomers of 1 inhibited ex vivo lipid peroxidation to an equal extent. Thus the in vivo uptake into myocytes (cardioselectivity) is independent of the geometry at the chiral center and common to permanently cationic compounds.