5-ethyl-3-(3-tributylstannyl)-2,5-dihydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: 5-ethyl-3-(3-tributylstannyl)-2,5-dihydrofuran-2-one
• 英文别名: 5-ethyl-3-(tributylstannyl)-2,5-dihydrofuran-2-one
• 化学式: C₁₈H₃₄O₂Sn
• 分子量: 401.177
• InChiKey: NFUOQROHOGVUJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-碘吡啶 、 5-ethyl-3-(3-tributylstannyl)-2,5-dihydrofuran-2-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到2-ethyl-4-(3-pyridyl)-2H-furan-5-one
  参考文献：
  名称：

  Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances

  摘要：

  一系列通过苯环连接到丁烯内酯核心的四唑类化合物，是通过α-(三丁基锡基)丁烯内酯和5-(烷基硫基)-1-(4-碘苯基)四唑的斯蒂尔偶联反应制备的，并且对这些化合物进行了抗真菌和细胞毒活性测试。有趣的抗真菌活性针对丝状菌株Absidia corymbifera，以及对白血病细胞HL-60和CCRF-CEM的细胞毒活性被发现。细胞毒活性需要丁烯内酯环和连接到四唑环的烷基硫基团同时存在。此外，还评估了与5-碘四唑进行Pd偶联反应的可行性。

  DOI：

  10.1135/cccc2009040

文献信息

• Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift
  作者：Jiří Kuneš、Vojtěch Balšánek、Milan Pour、Vladimír Buchta

  DOI：10.1135/cccc20011809

  日期：——

  In continuing the studies on the synthesis and evaluation of antifungal activity of the analogues of (-)incrustoporine, the replacement of the phenyl moiety at C3 of the furanone ring with a hetaryl substituent was considered. Thus, a series of 5-alkyl-3-hetaryl-2,5-dihydrofuran-2-ones with the thienyl, furyl and thiazolyl moieties attached to C3 was synthesized, and the compounds subjected to antifungal activity screening. In the preparation of compounds containing the oxazolyl fragment, the [2,3]-sigmatropic rearrangement led to the fragmentation of the oxazole ring, resulting in the formation of 3-(1-benzamido-2-oxoethylidene)-5-methyltetrahydrofuran-2-one. Somewhat surprisingly, the antifungal efficiency of the derivatives was lower in comparison with analogues containing a substituted phenyl at C3.

  在继续对(-)incrustoporine的类似物进行合成和抗真菌活性评估的研究中，考虑了在呋喃酮环的C3位置用杂环取代基取代苯基的替换。因此，合成了一系列连接到C3的噻吩基、呋喃基和噻唑基的5-烷基-3-杂环-2,5-二氢呋喃-2-酮，并对这些化合物进行了抗真菌活性筛选。在含有噁唑基片段的化合物制备过程中，[2,3]-sigmatropic重排导致噁唑环的断裂，形成了3-(1-苯甲酰胺基-2-氧乙烯基)-5-甲基四氢呋喃-2-酮。令人惊讶的是，与含有取代苯基的类似物相比，这些衍生物的抗真菌效果较低。
• 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.
• Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances
  作者：Vojtěch Balšánek、Lucie Tichotová、Jiří Kuneš、Marcel Špulák、Milan Pour、Ivan Votruba、Vladimír Buchta

  DOI：10.1135/cccc2009040

  日期：——

  A series of tetrazoles linked to the butenolide core via benzene rings were prepared by the Stille coupling reaction of α-(tributylstannyl)butenolides and 5-(alkylsulfanyl)-1-(4-iodophenyl)tetrazoles, and the compounds were tested for antifungal and cytostatic activity. Interesting antifungal activities against the filamentous strain Absidia corymbifera, and cytostatic activities against leukemic cells HL-60 and CCRF-CEM were found. The cytostatic activity requires the presence of both the butenolide ring and the alkylsulfanyl group bound to tetrazole ring. In addition, the feasibility of Pd-coupling reactions with 5-iodotetrazoles was evaluated.

  一系列通过苯环连接到丁烯内酯核心的四唑类化合物，是通过α-(三丁基锡基)丁烯内酯和5-(烷基硫基)-1-(4-碘苯基)四唑的斯蒂尔偶联反应制备的，并且对这些化合物进行了抗真菌和细胞毒活性测试。有趣的抗真菌活性针对丝状菌株Absidia corymbifera，以及对白血病细胞HL-60和CCRF-CEM的细胞毒活性被发现。细胞毒活性需要丁烯内酯环和连接到四唑环的烷基硫基团同时存在。此外，还评估了与5-碘四唑进行Pd偶联反应的可行性。