[1-acetyloxy-6-[(E)-[(4-fluorophenyl)hydrazinylidene]methyl]-9-oxoxanthen-3-yl] acetate | 959316-03-1

• 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: [1-acetyloxy-6-[(E)-[(4-fluorophenyl)hydrazinylidene]methyl]-9-oxoxanthen-3-yl] acetate
• CAS: 959316-03-1
• 化学式: C₂₄H₁₇FN₂O₆
• 分子量: 448.407
• InChiKey: OEZGPSLHVQFDCE-RPPGKUMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [1-acetyloxy-6-[(E)-[(4-fluorophenyl)hydrazinylidene]methyl]-9-oxoxanthen-3-yl] acetate 在 碳酸氢钠 作用下， 以 丙醇 为溶剂， 以66%的产率得到6-[(E)-[(4-fluorophenyl)hydrazinylidene]methyl]-1,3-dihydroxyxanthen-9-one
  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：

  6-bromomethyl-9-oxo-9H-xanthene-1,3-diyl diacetate 在 tetra(n-butyl)ammonium dichromate(VI) 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 [1-acetyloxy-6-[(E)-[(4-fluorophenyl)hydrazinylidene]methyl]-9-oxoxanthen-3-yl] acetate
  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