methyl 2-(4-fluorophenyl)pent-4-enoate | 67031-08-7

• 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: methyl 2-(4-fluorophenyl)pent-4-enoate
• 英文别名: Methyl-2-(p-fluorphenyl)-4-pentenoat
• CAS: 67031-08-7
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: OSMQOTBTGUPQAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-fluorophenyl)pent-4-enoate 在 溴 、 臭氧 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 Methyl-2-(p-fluorphenyl)-3-formylacrylat
  参考文献：
  名称：

  Antineoplastic agents. 58. Synthesis of 3-aryl-5-bromo-2(5H)-furanones

  摘要：

  DOI：

  10.1021/jo00415a028
• 作为产物：
  描述：

  4-氟苯乙酸 在 lithium diisopropyl amide 作用下， 生成 methyl 2-(4-fluorophenyl)pent-4-enoate
  参考文献：
  名称：

  3-Phenyl-5-methyl-2H,5H-furan-2-ones: tuning antifungal activity by varying substituents on the phenyl ring

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00376-0

文献信息

• 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.
• EDGAR M. T.; PETTIT G. R.; SMITH T. H., J. ORG. CHEM., 1978, 43, NO 21, 4115-4120
  作者：EDGAR M. T.、 PETTIT G. R.、 SMITH T. H.

  DOI：——

  日期：——
• 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
  作者：Milan Pour、Marcel Špulák、Vojtěch Balšánek、Jiřı́ Kuneš、Petra Kubanová、Vladimı́r Buchta

  DOI：10.1016/s0968-0896(03)00220-7

  日期：2003.7

  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.
• Antineoplastic agents. 58. Synthesis of 3-aryl-5-bromo-2(5H)-furanones
  作者：Mark T. Edgar、George R. Pettit、Thomas H. Smith

  DOI：10.1021/jo00415a028

  日期：1978.10