Acetic acid 3-acetoxy-5-bromomethyl-2,4-dichloro-9-oxo-9H-xanthen-1-yl ester | 462654-14-4

• 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: Acetic acid 3-acetoxy-5-bromomethyl-2,4-dichloro-9-oxo-9H-xanthen-1-yl ester
• 英文别名: [3-Acetyloxy-5-(bromomethyl)-2,4-dichloro-9-oxoxanthen-1-yl] acetate
• CAS: 462654-14-4
• 化学式: C₁₈H₁₁BrCl₂O₆
• 分子量: 474.092
• InChiKey: WVLWTOGJHKKRQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-acetoxy-5-bromomethyl-2,4-dichloro-9-oxo-9H-xanthen-1-yl ester 在 tetra(n-butyl)ammonium dichromate(VI) 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以26%的产率得到6,8-diacetoxy-5,7-dichloro-9-oxo-9H-xanthene-4-carboxaldehyde
  参考文献：
  名称：

  (2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species

  摘要：

  A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01332-0
• 作为产物：
  描述：

  2,4-dichloro-1,3-dihydroxy-5-methylxanthen-9-one 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 Acetic acid 3-acetoxy-5-bromomethyl-2,4-dichloro-9-oxo-9H-xanthen-1-yl ester
  参考文献：
  名称：

  (2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species

  摘要：

  A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01332-0