7-Bromo-4a-methoxy-xanthene-2,9-dione | 1350515-81-9

• 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-Bromo-4a-methoxy-xanthene-2,9-dione
• 英文别名: 7-bromo-4a-methoxyxanthene-2,9-dione
• CAS: 1350515-81-9
• 化学式: C₁₄H₉BrO₄
• 分子量: 321.127
• InChiKey: ZVMSMLXSDOAWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Bromo-4a-methoxy-xanthene-2,9-dione 以 乙二醇二甲醚 为溶剂， 反应 0.17h， 以10%的产率得到7-bromo-2-hydroxyxanthone
  参考文献：
  名称：

  The synthesis of xanthones, xanthenediones, and spirobenzofurans: Their antibacterial and antifungal activity

  摘要：

  Exposure of the phenol, (5-bromo-2-hydroxyphenyl)(2,4,5-trimethoxyphenyl)methanone 18 to ceric ammonium nitrate (CAN) resulted in the formation of 7-bromo-3,4a-dimethoxy-2H-xanthene-2,9( 4aH)-dione 19 and 5-bromo-2',5'-dimethoxy-3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione 20. The brominated spirobenzofuran 20 was then subjected to Suzuki-Miyaura reactions to give six derivatives 22a-f. These compounds, related diones and xanthones displayed mostly noteworthy antimicrobial activity, particularly towards the yeasts Cryptococcus neoformans and Candida albicans. Diones 15 and 30 displayed significant activity (7.8 mu g/mL) against C. albicans and C. neoformans, respectively. Furthermore, dione 10 displayed the most significant activity (3.6 mu g/mL) against both yeasts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.088
• 作为产物：
  描述：

  (5-bromo-2-hydroxyphenyl)(2,5-dimethoxyphenyl)methanone 在 ammonium cerium (IV) nitrate 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 0.17h， 以45%的产率得到7-Bromo-4a-methoxy-xanthene-2,9-dione
  参考文献：
  名称：

  The synthesis of xanthones, xanthenediones, and spirobenzofurans: Their antibacterial and antifungal activity

  摘要：

  Exposure of the phenol, (5-bromo-2-hydroxyphenyl)(2,4,5-trimethoxyphenyl)methanone 18 to ceric ammonium nitrate (CAN) resulted in the formation of 7-bromo-3,4a-dimethoxy-2H-xanthene-2,9( 4aH)-dione 19 and 5-bromo-2',5'-dimethoxy-3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione 20. The brominated spirobenzofuran 20 was then subjected to Suzuki-Miyaura reactions to give six derivatives 22a-f. These compounds, related diones and xanthones displayed mostly noteworthy antimicrobial activity, particularly towards the yeasts Cryptococcus neoformans and Candida albicans. Diones 15 and 30 displayed significant activity (7.8 mu g/mL) against C. albicans and C. neoformans, respectively. Furthermore, dione 10 displayed the most significant activity (3.6 mu g/mL) against both yeasts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.088

文献信息

• The synthesis of xanthones, xanthenediones, and spirobenzofurans: Their antibacterial and antifungal activity
  作者：Justin J. Omolo、Myron M. Johnson、Sandy F. van Vuuren、Charles B. de Koning

  DOI：10.1016/j.bmcl.2011.09.088

  日期：2011.12

  Exposure of the phenol, (5-bromo-2-hydroxyphenyl)(2,4,5-trimethoxyphenyl)methanone 18 to ceric ammonium nitrate (CAN) resulted in the formation of 7-bromo-3,4a-dimethoxy-2H-xanthene-2,9( 4aH)-dione 19 and 5-bromo-2',5'-dimethoxy-3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione 20. The brominated spirobenzofuran 20 was then subjected to Suzuki-Miyaura reactions to give six derivatives 22a-f. These compounds, related diones and xanthones displayed mostly noteworthy antimicrobial activity, particularly towards the yeasts Cryptococcus neoformans and Candida albicans. Diones 15 and 30 displayed significant activity (7.8 mu g/mL) against C. albicans and C. neoformans, respectively. Furthermore, dione 10 displayed the most significant activity (3.6 mu g/mL) against both yeasts. (C) 2011 Elsevier Ltd. All rights reserved.