3-Hydroxy-1,6,8-trimethoxy-naphthalene-2-carboxylic Acid Methyl Ester | 505052-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Hydroxy-1,6,8-trimethoxy-naphthalene-2-carboxylic Acid Methyl Ester
• 英文别名: 3-Hydroxy-1,6,8-trimethoxy-naphthalin-2-carbonsaeure-methylester；Methyl 3-hydroxy-1,6,8-trimethoxy-2-naphthoate；methyl 3-hydroxy-1,6,8-trimethoxynaphthalene-2-carboxylate
• CAS: 505052-96-0
• 化学式: C₁₅H₁₆O₆
• 分子量: 292.288
• InChiKey: ZLNMNGRUJUXMLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-1,6,8-trimethoxy-naphthalene-2-carboxylic Acid Methyl Ester 在 吡啶 、 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 salcomine 、 四乙基氯化铵 、 氧气 、 sodium acetate 、 三溴化硼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone
  参考文献：
  名称：

  Novel Total Synthesis of the 2-Azaanthraquinone Alkaloid Scorpinone Using a Tandem Oxidation and Azaelectrocyclic Reaction

  摘要：

  A new tandem oxidation and electrocyclic reaction of a 1-aza 6 pi-electron system derived from a known 3-hydroxynaphthalene derivative was developed for the synthesis of 2-azaanthraquinones. Total synthesis of scorpinone (1a) was achieved in seven steps using this new tandem reaction. In addition, the positional isomer, 7,9-dimethoxy-4-methylbenzo[g]isoquinoline-5,10-dione (1b) was also synthesized in the same way.

  DOI：

  10.3987/com-14-13155
• 作为产物：
  描述：

  methyl 1,3-dihydroxy-6,8-dimethoxynaphthalene-2-carboxylate 在 咪唑 、 potassium fluoride 、 氢溴酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 30.75h， 生成 3-Hydroxy-1,6,8-trimethoxy-naphthalene-2-carboxylic Acid Methyl Ester
  参考文献：
  名称：

  Synthetic Approach to Hypoxyxylerone, Novel Inhibitor of Topoisomerase I

  摘要：

  [GRAPHICS]A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to date in natural product synthesis and employed here for the first time with a dinaphthalenic substrate, to access the pentacyclic system of hypoxyxylerone.

  DOI：

  10.1021/ol026454d

文献信息

• Process for the manufacture of hypoxyxylerone derivatives
  申请人：Aventis Pharma S.A.

  公开号：EP1300403A1

  公开（公告）日：2003-04-09

  The present invention relates to the total synthesis of hypoxyxylerone derivatives (formula I) and their biological activities. R1-R5 are as described in the description.

  本发明涉及对hypoxyxylerone衍生物（式I）的全合成及其生物活性。其中R1-R5的定义见说明书。
• Synthetic Approach to Hypoxyxylerone, Novel Inhibitor of Topoisomerase I
  作者：Arnaud Piettre、Emmanuel Chevenier、Christine Massardier、Yves Gimbert、Andrew E. Greene

  DOI：10.1021/ol026454d

  日期：2002.9.1

  [GRAPHICS]A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to date in natural product synthesis and employed here for the first time with a dinaphthalenic substrate, to access the pentacyclic system of hypoxyxylerone.
• Novel Total Synthesis of the 2-Azaanthraquinone Alkaloid Scorpinone Using a Tandem Oxidation and Azaelectrocyclic Reaction
  作者：Satoshi Hibino、Tominari Choshi、Miharu Hironaka、Miki Goto、Kaori Shimizu、Yuhki Kurata、Takashi Nishiyama、Noriyuki Hatae

  DOI：10.3987/com-14-13155

  日期：——

  A new tandem oxidation and electrocyclic reaction of a 1-aza 6 pi-electron system derived from a known 3-hydroxynaphthalene derivative was developed for the synthesis of 2-azaanthraquinones. Total synthesis of scorpinone (1a) was achieved in seven steps using this new tandem reaction. In addition, the positional isomer, 7,9-dimethoxy-4-methylbenzo[g]isoquinoline-5,10-dione (1b) was also synthesized in the same way.

表征谱图