8-hydroxy-1,3,9,11-tetramethoxy-6-methoxymethyl-14-oxa-benzo[α]naphthacen-7-one | 468078-70-8

• 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: 8-hydroxy-1,3,9,11-tetramethoxy-6-methoxymethyl-14-oxa-benzo[α]naphthacen-7-one
• 英文别名: 15-Hydroxy-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-13-one
• CAS: 468078-70-8
• 化学式: C₂₇H₂₄O₈
• 分子量: 476.483
• InChiKey: LGMJCYBYMMRJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-hydroxy-1,3,9,11-tetramethoxy-6-methoxymethyl-14-oxa-benzo[α]naphthacen-7-one 在 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到1,3,9,11-tetramethoxy-6-methoxymethyl-7H-14-oxa-benzo[α]naphthacen-8-ol
  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 、 potassium fluoride 、 氢氧化钾 、 正丁基锂 、 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 254.75h， 生成 8-hydroxy-1,3,9,11-tetramethoxy-6-methoxymethyl-14-oxa-benzo[α]naphthacen-7-one
  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

• An Anionic Polycondensation Strategy for the Synthesis of Dibenzo­xanthenones: Progress Toward the Synthesis of Hypoxyxylerone
  作者：Yves Gimbert、Emmanuel Chevenier、Christophe Lucatelli、Urvish Pandya、Wei Wang、Andrew Greene

  DOI：10.1055/s-2004-835634

  日期：——

  An anionic polycondensation has been used as the key step in a highly convergent strategy for the preparation of hypoxy­xylerone derivatives.

  一种阴离子缩聚反应已被用作高度收敛策略中的关键步骤，用于制备假氧木酮衍生物。
• 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.