7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one | 39838-86-3

• 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: 7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one
• 英文别名: 7-hydroxy-1,3-dimethoxyxanthen-9-one；7-hydroxy-1,3-dimethoxy-xanthen-9-one；1,3-Dimethoxy-7-hydroxyxanthon
• CAS: 39838-86-3
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: AKHIWMMZYTUQOE-UHFFFAOYSA-N

物化性质

• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 nigrolineaxanthone F
  参考文献：
  名称：

  Facile Synthesis of 1,3,7-Trihydroxyxanthone and Its Regioselective Coupling Reactions with Prenal:  Simple and Efficient Access to Osajaxanthone and Nigrolineaxanthone F

  摘要：

  A facile five-step synthesis of naturally occurring 1,3,7-trihydroxyxanthone has been described starting from 1,3,5-trimethoxybenzene via NBS-induced nuclear bromination, lithiation followed by an in situ benzoylation with methyl 2,5-dibenzyloxybenzoate, selective deprotection of the two benzyl groups, base-catalyzed intramolecular cyclization, and demethylations pathway with 62% overall yield. The regioselective coupling reactions of 1,3,7-trihydroxyxanthone with prenal in the presence of calcium hydroxide at room temperature and under thermal conditions at 140-150 degrees C have been demonstrated to exclusively obtain the natural products osajaxanthone in 75% yield and nigrolineaxanthone F in 98% yield, respectively.

  DOI：

  10.1021/jo0606655
• 作为产物：
  描述：

  (2,5-dibenzyloxyphenyl)(2,4,6-trimethoxyphenyl)methanone 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、448.16 kPa 条件下， 反应 36.0h， 生成 7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Facile Synthesis of 1,3,7-Trihydroxyxanthone and Its Regioselective Coupling Reactions with Prenal:  Simple and Efficient Access to Osajaxanthone and Nigrolineaxanthone F

  摘要：

  A facile five-step synthesis of naturally occurring 1,3,7-trihydroxyxanthone has been described starting from 1,3,5-trimethoxybenzene via NBS-induced nuclear bromination, lithiation followed by an in situ benzoylation with methyl 2,5-dibenzyloxybenzoate, selective deprotection of the two benzyl groups, base-catalyzed intramolecular cyclization, and demethylations pathway with 62% overall yield. The regioselective coupling reactions of 1,3,7-trihydroxyxanthone with prenal in the presence of calcium hydroxide at room temperature and under thermal conditions at 140-150 degrees C have been demonstrated to exclusively obtain the natural products osajaxanthone in 75% yield and nigrolineaxanthone F in 98% yield, respectively.

  DOI：

  10.1021/jo0606655

文献信息

• Synthesis and in vitro antitumor activities of xanthone derivatives containing 1,4-disubstituted-1,2,3-triazole moiety
  作者：Yan Zou、Qingjie Zhao、Honggang Hu、Lina Hu、Shichong Yu、Mingjuan Xu、Qiuye Wu

  DOI：10.1007/s12272-012-1206-4

  日期：2012.12

  To explore the more active antitumor compounds, two series of new xanthones, containing 1,4-disubstituted-1,2,3-triazole moiety were designed and synthesized. Eaton’s Reagent and “click reaction” were used in the synthesis. Most of the title compounds showed good inhibitory activity against the hepatoma carcinoma cell line (Bel-7402) and human cervical carcinoma cell line (HeLa) in vitro. Compounds

  为了探索更具活性的抗肿瘤化合物，设计并合成了两个系列的含有 1,4-二取代-1,2,3-三唑部分的新型氧杂蒽酮。合成中使用了伊顿试剂和“点击反应”。大多数标题化合物在体外对肝癌细胞系 (Bel-7402) 和人宫颈癌细胞系 (HeLa) 显示出良好的抑制活性。化合物 10a、10e、10f、11r 和 11t 具有强活性，IC50 值范围为 2.2 ± 0.17 至 7.1 ± 0.27 ∝M，相当于阿霉素。