3-benzyloxy-1,6,8-trimethoxy-naphthalene-2-carboxylic acid 3-bromo-4,5,7-trimethoxy-naphthalen-2-yl methyl ester | 468078-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-benzyloxy-1,6,8-trimethoxy-naphthalene-2-carboxylic acid 3-bromo-4,5,7-trimethoxy-naphthalen-2-yl methyl ester
• 英文别名: (3-bromo-4,5,7-trimethoxynaphthalen-2-yl)methyl 1,6,8-trimethoxy-3-phenylmethoxynaphthalene-2-carboxylate
• CAS: 468078-48-0
• 化学式: C₃₅H₃₃BrO₉
• 分子量: 677.546
• InChiKey: ASJNMKSIRKMIHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-1,6,8-trimethoxy-naphthalene-2-carboxylic acid 3-bromo-4,5,7-trimethoxy-naphthalen-2-yl methyl ester 在 palladium dihydroxide 氢氧化钾 、 正丁基锂 、 dimethyl sulfide borane 、 氢气 、 lithium chloride 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 247.0h， 生成 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 咪唑 、 potassium fluoride 、 氢氧化钾 、 氢溴酸 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 55.75h， 生成 3-benzyloxy-1,6,8-trimethoxy-naphthalene-2-carboxylic acid 3-bromo-4,5,7-trimethoxy-naphthalen-2-yl 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。
• Efficient Preparation of Polysubstituted Naphthyl Phenyl and Dinaphthyl Ketones from Naphthalenic Esters by Anionic Homo-Fries Rearrangement
  作者：Yves Gimbert、Andrew E. Greene、Arnaud Piettre、Christine Massardier、Emmanuel Chevenier

  DOI：10.1055/s-2002-35601

  日期：——

  The anionic homo-Fries rearrangement of naphthalenic esters can be effected in good yield to provide regiocontrolled access to complex diaryl ketones.

  萘酯的阴离子均-弗赖斯重排可以以良好的产率进行，以提供对复杂二芳基酮的区域控制访问。
• 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.