5-methyl-3-(4-bromo-1-naphthyl)tetrahydrofuran-2-one | 619323-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-methyl-3-(4-bromo-1-naphthyl)tetrahydrofuran-2-one
• 英文别名: 3-(4-bromonaphthalen-1-yl)-5-methyloxolan-2-one
• CAS: 619323-52-3
• 化学式: C₁₅H₁₃BrO₂
• 分子量: 305.171
• InChiKey: IHDQGXKZDBBXSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(4-bromo-1-naphthyl)tetrahydrofuran-2-one 在 正丁基锂 、 苯基氯化硒 、 二异丙胺 、 双氧水 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 以19%的产率得到4-(4-bromo-1-naphthyl)-2-methyl-2H-furan-5-one
  参考文献：
  名称：

  Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group

  摘要：

  Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00220-7
• 作为产物：
  描述：

  methyl 2-(4-bromo-1-naphthyl)pent-4-enoate 在 lithium hydroxide 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 20.33h， 生成 5-methyl-3-(4-bromo-1-naphthyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group

  摘要：

  Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00220-7