3-(3,4-Dichloro-phenyl)-5-hydroxymethyl-dihydro-furan-2-one | 362483-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3,4-Dichloro-phenyl)-5-hydroxymethyl-dihydro-furan-2-one
• 英文别名: 3-(3,4-Dichlorophenyl)-5-(hydroxymethyl)oxolan-2-one
• CAS: 362483-73-6
• 化学式: C₁₁H₁₀Cl₂O₃
• 分子量: 261.105
• InChiKey: KPCMVWBMZPKAEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-Dichloro-phenyl)-5-hydroxymethyl-dihydro-furan-2-one 在 吡啶 、 咪唑 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.5h， 生成 2,2-Dimethyl-propionic acid 4-(3,4-dichloro-phenyl)-5-oxo-2,5-dihydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs

  摘要：

  3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34,mug/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 mug/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

  DOI：

  10.1021/jm010155x
• 作为产物：
  描述：

  2-(3,4-dichlorophenyl)-pent-4-enoic acid 在 57percent MCPBA 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 3-(3,4-Dichloro-phenyl)-5-hydroxymethyl-dihydro-furan-2-one
  参考文献：
  名称：

  3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs

  摘要：

  3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34,mug/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 mug/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

  DOI：

  10.1021/jm010155x