1-溴-3-羟基蒽醌 | 733016-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-溴-3-羟基蒽醌
• 英文名称: 1-bromo-3-hydroxyanthraquinone
• 英文别名: 1-Bromo-3-hydroxyanthracene-9,10-dione；1-bromo-3-hydroxyanthracene-9,10-dione
• CAS: 733016-60-9
• 化学式: C₁₄H₇BrO₃
• 分子量: 303.112
• InChiKey: KYNZJDCJGYIDFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯酐 、 间溴苯酚 在 三氯化铝 、 sodium chloride 作用下， 反应 0.75h， 生成 3-bromo-1-hydroxyanthraquinone 、 1-溴-3-羟基蒽醌 、 1-羟基蒽醌 、 1-溴-4-羟基蒽醌
  参考文献：
  名称：

  路易斯酸催化弗里德尔中的卤代苯酚重排 - 工艺条件：竞争性初始质子化和酰化的证据

  摘要：

  在路易斯酸催化的邻苯二甲酸酐与溴酚或溴苯甲醚的傅克反应过程中观察到卤素重排。进一步研究表明，在这些反应条件下，2-、3-和 4-溴酚会重排成其他异构体。这些反应的产物分布表明卤素重排发生在缩合步骤的 s-配合物中间体期间。此外，碘苯酚会迅速加氢脱碘而不是重排，而氯苯酚根本不会重排。

  DOI：

  10.1071/ch08084

文献信息

• Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
  作者：Koushik Saha、Kok Wai Lam、Faridah Abas、A. Sazali Hamzah、Johnson Stanslas、Lim Siang Hui、Nordin H. Lajis

  DOI：10.1007/s00044-012-0197-5

  日期：2013.5

  Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 mu M. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.