6-acetyl-2,7-dihydroxy-5-methylnaphthalene-1,4-dione | 1384166-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-acetyl-2,7-dihydroxy-5-methylnaphthalene-1,4-dione
• CAS: 1384166-98-6
• 化学式: C₁₃H₁₀O₅
• 分子量: 246.219
• InChiKey: OIEMJYCFMMMSHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  91.67
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-acetyl-2,7-dihydroxy-5-methylnaphthalene-1,4-dione 在 glucose dehydrogenase 、 葡萄糖 、 1,3,6,8-tetrahydroxynaphthalene reductase 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以60%的产率得到(3S,4R)-7-acetyl-3,4,6-trihydroxy-8-methyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Biomimetic Asymmetric Synthesis of (R)-GTRI-02 and (3S,4R)-3,4-Dihydroxy-3,4-dihydronaphthalen-1(2H)-ones

  摘要：

  The NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) from Magnaporthe grisea was used for the biomimetic synthesis of (R)-GTRI-02 by stereoselective reduction of 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone. This also led to the isolation of a (3S,4R)-cis-ketodiol formed by T4HNR-catalyzed reduction of the corresponding hydroxynaphthoquinone. Flaviolin and lawsone also reduced to corresponding cis-ketodiols in good yields.

  DOI：

  10.1021/ol301305p
• 作为产物：
  描述：

  1-(3-hydroxy-6,8-dimethoxy-1-methylnaphthalen-2-yl)ethanone 在 氧气 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 6-acetyl-2,7-dihydroxy-5-methylnaphthalene-1,4-dione
  参考文献：
  名称：

  Biomimetic Asymmetric Synthesis of (R)-GTRI-02 and (3S,4R)-3,4-Dihydroxy-3,4-dihydronaphthalen-1(2H)-ones

  摘要：

  The NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) from Magnaporthe grisea was used for the biomimetic synthesis of (R)-GTRI-02 by stereoselective reduction of 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone. This also led to the isolation of a (3S,4R)-cis-ketodiol formed by T4HNR-catalyzed reduction of the corresponding hydroxynaphthoquinone. Flaviolin and lawsone also reduced to corresponding cis-ketodiols in good yields.

  DOI：

  10.1021/ol301305p