3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6,8-dimethoxy-naphthalene-2-carboxylic Acid Methyl Ester | 505052-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6,8-dimethoxy-naphthalene-2-carboxylic Acid Methyl Ester
• 英文别名: Methyl 3-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-6,8-dimethoxynaphthalene-2-carboxylate
• CAS: 505052-95-9
• 化学式: C₂₀H₂₈O₆Si
• 分子量: 392.524
• InChiKey: CKEPWVSYGYVKLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6,8-dimethoxy-naphthalene-2-carboxylic Acid Methyl Ester 在 palladium dihydroxide potassium fluoride 、 氢氧化钾 、 正丁基锂 、 氢溴酸 、 氢气 、 potassium carbonate 、 三苯基膦 、 silver(l) oxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 227.75h， 生成 1-(3-hydroxy-1,6,8-trimethoxy-naphthalen-2-yl)-1-(1,6,8-trimethoxy-3-methoxymethyl-naphthalen-2-yl)-methanone
  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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 methyl 1,3-dihydroxy-6,8-dimethoxynaphthalene-2-carboxylate 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6,8-dimethoxy-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

• 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.