5-(1,3-Benzodioxol-5-yl)-6'-hydroxy-1',4'-dimethoxy-spiro[benzofuran-2,3'-cyclohexa-1,4-diene]-3-one | 1350515-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(1,3-Benzodioxol-5-yl)-6'-hydroxy-1',4'-dimethoxy-spiro[benzofuran-2,3'-cyclohexa-1,4-diene]-3-one
• 英文别名: 5-(1,3-benzodioxol-5-yl)-6'-hydroxy-1',4'-dimethoxyspiro[1-benzofuran-2,3'-cyclohexa-1,4-diene]-3-one
• CAS: 1350515-93-3
• 化学式: C₂₂H₁₈O₇
• 分子量: 394.381
• InChiKey: UAGMWZCUVFUKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 四(三苯基膦)钯 、 ammonium cerium (IV) nitrate 、 5%-palladium/activated carbon 、 氢气 、 cesium fluoride 作用下， 以 乙二醇二甲醚 、 氯仿 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 20.0~150.0 ℃ 、101.33 kPa 条件下， 反应 24.34h， 生成 5-(1,3-Benzodioxol-5-yl)-6'-hydroxy-1',4'-dimethoxy-spiro[benzofuran-2,3'-cyclohexa-1,4-diene]-3-one
  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.