4-(4-methoxyphenyl)-2-methyl-2H-furan-5-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-2-methyl-2H-furan-5-one
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BJWLLZGXINITLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-methoxyphenyl)pent-4-enoic acid 在 氢溴酸 、 sodium carbonate 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 生成 4-(4-methoxyphenyl)-2-methyl-2H-furan-5-one
  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

• 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.
• First Iodine-Catalyzed Deallylation of Reactive Allyl Methylene Esters
  作者：Beena R. Nawghare、Pradeep D. Lokhande

  DOI：10.1080/00397911.2012.682245

  日期：2013.7.18

  C-Allyl cleavage has been developed using the inexpensive and mild reagent iodine in dimethylsulfoxide. A variety of compounds with active methylene groups were C-deallylated using this reagent. This method is efficient and operationally simple in comparison to the methods using transition-metal complexes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Regioselective Pd-catalyzed alkylative lactonizations of 4-hydroxy-2-alkynecarboxylates with organoboronic acids
  作者：Chang Ho Oh、Su Jin Park、Jin Hyang Ryu、Arun Kumar Gupta

  DOI：10.1016/j.tetlet.2004.07.129

  日期：2004.9

  The palladium-catalyzed addition of aryl- and alkenylboronic acids to 4-hydroxy-2-alkynecarboxylates and in situ lactonization would constitute a novel methodology for the synthesis of various butenolides with an excellent stereoselectivity and a high control of regioselectivity. (C) 2004 Published by Elsevier Ltd.