3-Hydroxy-6,8-dimethoxy-1-methyl-naphthalin-2-carbonsaeure-ethylester | 17276-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Hydroxy-6,8-dimethoxy-1-methyl-naphthalin-2-carbonsaeure-ethylester
• 英文别名: Ethyl 3-hydroxy-6,8-dimethoxy-1-methyl-2-naphthoate；ethyl 3-hydroxy-6,8-dimethoxy-1-methylnaphthalene-2-carboxylate
• CAS: 17276-11-8
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: MSNMOZQVYDYKGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-6,8-dimethoxy-1-methyl-naphthalin-2-carbonsaeure-ethylester 、 甲基锂 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.17h， 以92%的产率得到1-(3-hydroxy-6,8-dimethoxy-1-methylnaphthalen-2-yl)ethanone
  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：

  2-(3,5-dimethoxyphenyl)acetyl chloride 在 甲烷磺酸 、 四磷十氧化物 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-Hydroxy-6,8-dimethoxy-1-methyl-naphthalin-2-carbonsaeure-ethylester
  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

• Metabolic Products of Fungi. XXVI. Synthesis of racemic Ustilaginoidin A and Its Related Compounds. (1). Synthesis of 2.2', 4.4', 5.5', 7.7'-Octamethoxy-1.1'-binaphthalene (=Product A Octamethyl Ether).
  作者：Eisaku Morishita、Shoji Shibata

  DOI：10.1248/cpb.15.1765

  日期：——

  Octamethyl ether of product A which was derived from ustilaginoidin A by alkaline degradation was synthesized by the Ullmann condensation of dimethyl ether of 5-bromo-6, 8-dimethyl-1, 3-naphthalenediol (XXI). Starting from 3, 5-dimethoxyphenylacetic acid (IX), the 2-bromo derivative (VII) was prepared which was C-acetylated to afford XX, and then cyclized to form a bromonaphthalene derivative (XXI), whose methyl ether is XXII. The position of C-C linkage connecting two monomeric moieties of ustilaginoidins has unequivocally been established. Rearrangement of bromine atom during the process of methylation of bromohydroxynaphthalenes and cyclization forming the naphthalene nucleus were also discussed.

  通过对 5-溴-6，8-二甲基-1，3-萘二醇的二甲醚（XXI）进行乌尔曼缩合，合成了产品 A 的八甲醚，该产品 A 是由乌司他嗪素 A 通过碱性降解而得到的。从 3，5-二甲氧基苯乙酸（IX）开始，制备出 2-溴衍生物（VII），经 C-乙酰化后得到 XX，然后环化形成溴萘衍生物（XXI），其甲基醚为 XXII。连接两个乌司他尼苷单体分子的 C-C 连接位置已经明确。此外，还讨论了溴羟萘甲基化过程中溴原子的重新排列以及形成萘核的环化过程。
• 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.

表征谱图