(3-Bromo-4,5,7-trimethoxy-naphthalen-2-yl)-methanol | 468078-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3-Bromo-4,5,7-trimethoxy-naphthalen-2-yl)-methanol
• 英文别名: (3-bromo-4,5,7-trimethoxynaphthalen-2-yl)methanol
• CAS: 468078-52-6
• 化学式: C₁₄H₁₅BrO₄
• 分子量: 327.175
• InChiKey: YSXLTCVYXRRTQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-Bromo-4,5,7-trimethoxy-naphthalen-2-yl)-methanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到2-bromo-3-(bromomethyl)-1,6,8-trimethoxynaphthalene
  参考文献：
  名称：

  Synthetic Studies toward A-74528

  摘要：

  A potentially biomimetic approach toward the complex polyketide A-74528 is described. It is based on highly substituted biaryl compounds, synthesized using advanced cross-coupling and condensation methodologies.

  DOI：

  10.1021/ol103117j
• 作为产物：
  描述：

  (E)-4-(3,5-dimethoxyphenyl)-3-(methoxycarbonyl)but-3-enoic acid 在 吡啶 、 甲醇 、 氢氧化钾 、 lithium aluminium tetrahydride 、 1,2,4-三甲氧基苯 、 溴 、 potassium acetate 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 34.58h， 生成 (3-Bromo-4,5,7-trimethoxy-naphthalen-2-yl)-methanol
  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.
• Synthetic Studies toward A-74528
  作者：Anastasia Hager、Dmitry Mazunin、Peter Mayer、Dirk Trauner

  DOI：10.1021/ol103117j

  日期：2011.3.18

  A potentially biomimetic approach toward the complex polyketide A-74528 is described. It is based on highly substituted biaryl compounds, synthesized using advanced cross-coupling and condensation methodologies.