trimethyl-(1,3,9,11-tetramethoxy-6-methoxymethyl-7H-14-oxabenzo[α]naphthacen-8-yloxy)-silane | 468078-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: trimethyl-(1,3,9,11-tetramethoxy-6-methoxymethyl-7H-14-oxabenzo[α]naphthacen-8-yloxy)-silane
• 英文别名: Trimethyl-[[5,7,17,19-tetramethoxy-11-(methoxymethyl)-2-oxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4,6,8,10,14,16,18,20-decaen-15-yl]oxy]silane
• CAS: 468078-80-0
• 化学式: C₃₀H₃₄O₇Si
• 分子量: 534.681
• InChiKey: CQDKWMBSNHOWPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trimethyl-(1,3,9,11-tetramethoxy-6-methoxymethyl-7H-14-oxabenzo[α]naphthacen-8-yloxy)-silane 在 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以20.4 mg的产率得到penta(O-methyl)hypoxyxylerone
  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：

  methyl 1,3-dihydroxy-6,8-dimethoxynaphthalene-2-carboxylate 在 palladium dihydroxide 咪唑 、 2,6-二甲基吡啶 、 potassium fluoride 、 氢氧化钾 、 正丁基锂 、 dimethyl sulfide borane 、 氢溴酸 、 氢气 、 potassium carbonate 、 三苯基膦 、 lithium chloride 、 silver(l) oxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 305.25h， 生成 trimethyl-(1,3,9,11-tetramethoxy-6-methoxymethyl-7H-14-oxabenzo[α]naphthacen-8-yloxy)-silane
  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.