methyl 2-(4-bromophenyl)pent-4-enoate | 362483-70-3

• 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-bromophenyl)pent-4-enoate
• CAS: 362483-70-3
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: WOOWNCBWPPKEGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-bromophenyl)pent-4-enoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 2-(p-bromophenyl)-4-pentenoic acid
  参考文献：
  名称：

  大环所有杂种：在烯丙基中心的替代揭示了[13] -Macrodilactones的构象动力学。

  摘要：

  大环大环化合物采用的形状在它们的反应性和与生物分子结合的能力中起作用。我们研究了作为天然产物大环化合物模型的[13]-大二内酯特定家族的合成，构象分析和性质。我们的大二内酯的特征使我们能够通过该大环族新成员的模块合成来研究立体中心与平面手性之间的关系。在这里，我们报道了从新的[13]-宏二内酯（该分子在邻近烯烃的位置上被取代）获得的见解。与α-取代的区域异构体相比，通过X射线晶体学，NMR耦合常数和计算化学反应对反应产物进行表征，可对该化合物进行分析，揭示了烯烃单元是动态的。也就是说，数据支持一个模型，其中我们的[13]-大二内酯中的烯烃在两个构象之间振荡。一种构象与另一种构象的反应性差异导致这种动态行为的表现。结果强调了在某些天然产物大环中观察到的局部构象动力学，这可能对生物分子结合有影响。

  DOI：

  10.1002/asia.201700997
• 作为产物：
  描述：

  对溴苯乙酸 在 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 methyl 2-(4-bromophenyl)pent-4-enoate
  参考文献：
  名称：

  大环所有杂种：在烯丙基中心的替代揭示了[13] -Macrodilactones的构象动力学。

  摘要：

  大环大环化合物采用的形状在它们的反应性和与生物分子结合的能力中起作用。我们研究了作为天然产物大环化合物模型的[13]-大二内酯特定家族的合成，构象分析和性质。我们的大二内酯的特征使我们能够通过该大环族新成员的模块合成来研究立体中心与平面手性之间的关系。在这里，我们报道了从新的[13]-宏二内酯（该分子在邻近烯烃的位置上被取代）获得的见解。与α-取代的区域异构体相比，通过X射线晶体学，NMR耦合常数和计算化学反应对反应产物进行表征，可对该化合物进行分析，揭示了烯烃单元是动态的。也就是说，数据支持一个模型，其中我们的[13]-大二内酯中的烯烃在两个构象之间振荡。一种构象与另一种构象的反应性差异导致这种动态行为的表现。结果强调了在某些天然产物大环中观察到的局部构象动力学，这可能对生物分子结合有影响。

  DOI：

  10.1002/asia.201700997

文献信息

• Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives
  作者：Petr Šenel、Lucie Tichotová、Ivan Votruba、Vladimír Buchta、Marcel Špulák、Jiří Kuneš、Milan Nobilis、Ondřej Krenk、Milan Pour

  DOI：10.1016/j.bmc.2010.01.030

  日期：2010.3

  parent furanone structure were therefore prepared and evaluated. In line with the ease of elimination of the substituent from C5, low activities of the 5-alkoxy compounds were observed. On the other hand, their 5-aryloxymethyl congeners were found to be capable of liberating the antifungally active 5-methylene furanone into the testing medium. The antifungal effect of the 5-alkylidene derivatives was

  发现先前描述为高度抗真菌活性的5-乙酰氧基甲基-3-（4-溴苯基）-2,5-二氢呋喃-2-酮可通过DMSO异常消除C5处的酯基来提供相应的5-亚甲基衍生物在抗真菌试验条件下。由于后者具有与最初报道的抗真菌作用几乎相同的抗真菌作用，因此5-乙酰氧基甲基呋喃酮仅用作实际的抗真菌活性物质的前体。因此，制备并评估了一系列在母体呋喃酮结构的C5处具有烷氧基，芳氧基和亚烷基取代基的化合物。与从C5中消除取代基的容易性相一致，观察到5-烷氧基化合物的活性低。另一方面，发现它们的5-芳氧基甲基同源物能够将抗真菌活性的5-亚甲基呋喃酮释放到测试介质中。5-亚烷基衍生物的抗真菌作用对亚烷基部分的取代高度敏感。为了保持化合物的高活性，在烯丙基位置的取代基是必需的。细胞抑制活性的并行评估显示抗真菌活性衍生物对HeLa S3和CCRF-CEM系的中等活性。用5-亚甲基-3-（4-溴苯基）-2,5-二氢呋喃-2-酮处
• 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.
• 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.
• 3-Phenyl-5-acyloxymethyl-2<i>H</i>,<i>5H</i>-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs
  作者：Milan Pour、Marcel Špulák、Vladimír Buchta、Petra Kubanová、Marie Vopršalová、Vladimír Wsól、Helena Fáková、Petr Koudelka、Hana Pourová、Radan Schiller

  DOI：10.1021/jm010155x

  日期：2001.8.1

  3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34,mug/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 mug/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.