(R)-7-acetyl-3,6-dihydroxy-8-methyltetralone | 217481-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-7-acetyl-3,6-dihydroxy-8-methyltetralone
• 英文别名: (R)-7-acetyl-3,6-dihydroxy-8-methyl-3,4-dihydronaphthalen-1(2H)-one；GTRI-02；(3R)-7-acetyl-3,6-dihydroxy-8-methyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 217481-71-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: ODXUROYZJHIZHE-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-7-acetyl-3,6-dihydroxy-8-methyltetralone 、 4-溴苯甲酰氯 以 吡啶 为溶剂， 反应 18.0h， 以53%的产率得到(R)-6-acetyl-5-methyl-4-oxo-1,2,3,4-tetrahydronaphthalene-2,7-diyl bis(4-bromobenzoate)
  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 glucose dehydrogenase 、 葡萄糖 、 1,3,6,8-tetrahydroxynaphthalene reductase 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 三溴化硼 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 48.0h， 生成 (R)-7-acetyl-3,6-dihydroxy-8-methyltetralone
  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

文献信息

• Biomimetic Asymmetric Synthesis of (<i>R</i>)-GTRI-02 and (3<i>S</i>,4<i>R</i>)-3,4-Dihydroxy-3,4-dihydronaphthalen-1(2<i>H</i>)-ones
  作者：Syed Masood Husain、Michael A. Schätzle、Caroline Röhr、Steffen Lüdeke、Michael Müller

  DOI：10.1021/ol301305p

  日期：2012.7.20

  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.