(3S,4R)-7-acetyl-3,4,6-trihydroxy-8-methyl-3,4-dihydronaphthalen-1(2H)-one | 1384166-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (3S,4R)-7-acetyl-3,4,6-trihydroxy-8-methyl-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: (3S,4R)-7-acetyl-3,4,6-trihydroxy-8-methyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1384166-97-5
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: GSCSYLBTHSNIMX-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-7-acetyl-3,4,6-trihydroxy-8-methyl-3,4-dihydronaphthalen-1(2H)-one 、 4-联苯硼酸 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (3aS,9bR)-7-acetyl-2-(biphenyl-4-yl)-8-hydroxy-6-methyl-3a,4-dihydronaphtho[1,2-d][1,3,2]dioxaborol-5(9bH)-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-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone 在 glucose dehydrogenase 、 葡萄糖 、 1,3,6,8-tetrahydroxynaphthalene reductase 、 氧气 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 39.0h， 生成 (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