3-(3,4-dichlorophenyl)-5-methyl-2,5-dihydrofuran-2-one | 301854-02-4

• 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-dichlorophenyl)-5-methyl-2,5-dihydrofuran-2-one
• 英文别名: 2(5H)-Furanone, 3-(3,4-dichlorophenyl)-5-methyl-；4-(3,4-dichlorophenyl)-2-methyl-2H-furan-5-one
• CAS: 301854-02-4
• 化学式: C₁₁H₈Cl₂O₂
• 分子量: 243.089
• InChiKey: CAHIYFYECGBERB-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  417.2±45.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3,4-dichlorophenyl)-pent-4-enoic acid 在 正丁基锂 、 苯基氯化硒 、 硫酸 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 3-(3,4-dichlorophenyl)-5-methyl-2,5-dihydrofuran-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

文献信息

• Microwave Assisted Suzuki Reactions for the Preparation of the Antifungal 3-Aryl-5-methyl-2,5-dihydrofuran-2-ones
  作者：Paul A. Worthington、Christopher J. Mathews、John Taylor、Melloney J. Tyte

  DOI：10.1055/s-2005-862367

  日期：——

  The Suzuki cross-coupling reaction of arylboronic acids with a bromo-furanone has been developed to prepare a series of substituted 2,5-dihydrofuran-2-ones related to the fungal metabolite, incrustoporin. A protocol of microwave heating was introduced to improve synthesis throughput.

  已开发了芳基硼酸与溴吡喃酮的铃木交叉耦合反应，以合成一系列与真菌代谢物incrustoporin相关的取代2,5-二氢呋喃-2-酮。引入了一种微波加热的方案，以提高合成效率。
• 3-Phenyl-5-methyl-2H,5H-furan-2-ones: tuning antifungal activity by varying substituents on the phenyl ring
  作者：Milan Pour、Marcel Špulák、Vojtěch Balšánek、Jiřı́ Kuneš、Vladimı́r Buchta、Karel Waisser

  DOI：10.1016/s0960-894x(00)00376-0

  日期：2000.8

  A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (-)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 3-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in mu mol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 mu mol/L). In terms of mu g/mL, the substance was more active (7.6 mu g/mL) than this standard antifungal drug (16.6 mu g/mL). (C) 2000 Elsevier Science Ltd. All rights reserved.