3-(4-methylphenyl)-5-methyltetrahydrofuran-2-one | 99593-46-1

• 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-(4-methylphenyl)-5-methyltetrahydrofuran-2-one
• 英文别名: trans-4-methyl-2-p-tolyl-γ-butyrolactone；5-Methyl-3-(4-methylphenyl)oxolan-2-one
• CAS: 99593-46-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XDQRUMRWDVQDAU-UHFFFAOYSA-N

物化性质

• 沸点：
  345.0±31.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)-5-methyltetrahydrofuran-2-one 在 正丁基锂 、 二异丙胺 、 苯基氯化硒 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 0.5h， 以39%的产率得到3-(4-methylphenyl)-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents

  摘要：

  On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in vivo. The small changes between 4 and 5 at the 3,4-position result in large differences in bioactivities. Compounds 4 exhibited significantly higher antiviral activity against tobacco mosaic virus (TMV) than dehydro compounds 5. However, the antifungal activity of 4 is relatively lower than that of 5. Compounds 4a, 4c, and 4i with excellent in vivo anti-TMV activity emerged as new antiviral lead compounds. Compounds 5d-g showed superiority over the commercial fungicides chlorothalonil and carbendazim against Cercospora arachidicola Hor at 50 mg kg(-1). The present study provides fundamental support for the development and optimization of (-)-incrustoporin derivatives as potential inhibitors of plant virus and pathogenic fungi.

  DOI：

  10.1021/jf503060k
• 作为产物：
  描述：

  对甲基苯乙酸 在 lithium hydroxide 、 硫酸 、 lithium diisopropyl amide 作用下， 生成 3-(4-methylphenyl)-5-methyltetrahydrofuran-2-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

• 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.
• JIX-XIAN, WANG;ALPER, H., J. ORG. CHEM., 1986, 51, N 2, 273-275
  作者：JIX-XIAN, WANG、ALPER, H.

  DOI：——

  日期：——
• Phase-transfer-catalyzed conversion of alkynes to lactones induced by manganese carbonyl complexes
  作者：Chin Hsien Wang、Howard Alper

  DOI：10.1021/jo00352a037

  日期：1986.1
• Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents
  作者：Aidang Lu、Jinjin Wang、Tengjiao Liu、Jian Han、Yinhui Li、Min Su、Jianxin Chen、Hui Zhang、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf503060k

  日期：2014.9.3

  On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in vivo. The small changes between 4 and 5 at the 3,4-position result in large differences in bioactivities. Compounds 4 exhibited significantly higher antiviral activity against tobacco mosaic virus (TMV) than dehydro compounds 5. However, the antifungal activity of 4 is relatively lower than that of 5. Compounds 4a, 4c, and 4i with excellent in vivo anti-TMV activity emerged as new antiviral lead compounds. Compounds 5d-g showed superiority over the commercial fungicides chlorothalonil and carbendazim against Cercospora arachidicola Hor at 50 mg kg(-1). The present study provides fundamental support for the development and optimization of (-)-incrustoporin derivatives as potential inhibitors of plant virus and pathogenic fungi.
• 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.