4,6-di(2-thienyl)-4,6-dihydro[1,3]dithio[4,5-c]furan-2-thione | 244066-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4,6-di(2-thienyl)-4,6-dihydro[1,3]dithio[4,5-c]furan-2-thione
• 英文别名: 4,6-bis(2-thienyl)-4,6-dihydrofuro[3,4-d]-1,3-dithiole-2-thione；4,6-Dithiophen-2-yl-4,6-dihydro-[1,3]dithiolo[4,5-c]furan-2-thione
• CAS: 244066-47-5
• 化学式: C₁₃H₈OS₅
• 分子量: 340.536
• InChiKey: VJGKDQMUVUSKOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-di(2-thienyl)-4,6-dihydro[1,3]dithio[4,5-c]furan-2-thione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以35%的产率得到4,6-bis(2-thienyl)furo[3,4-d]-1,3-dithiole-2-thione
  参考文献：
  名称：

  Novel Terthiophene and Bis(thienyl)furan Derivatives as Precursors to Highly Electroactive Polymers

  摘要：

  The syntheses of a series of 1,3-dithiole-2-thione derivatives (3-6), bearing fused terthiophene or bis(2-thienyl)-2,5-furan units, are reported. These novel heterocycles are readily polymerized electrochemically to give stable electroactive materials. The target compounds were obtained in moderate to high yield via the cyclization of the corresponding diketones or hydroxyketones, using phosphorus pentasulfide or acidic conditions. The ketones 12 and 17 were prepared directly from their hydroxy precursors by treatment with MnO2. The trans configuration of diketone 20 was confirmed by X-ray crystallography.

  DOI：

  10.1021/jo990198+
• 作为产物：
  描述：

  4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以14%的产率得到4,6-di(2-thienyl)-4,6-dihydro[1,3]dithio[4,5-c]furan-2-thione
  参考文献：
  名称：

  Novel Terthiophene and Bis(thienyl)furan Derivatives as Precursors to Highly Electroactive Polymers

  摘要：

  The syntheses of a series of 1,3-dithiole-2-thione derivatives (3-6), bearing fused terthiophene or bis(2-thienyl)-2,5-furan units, are reported. These novel heterocycles are readily polymerized electrochemically to give stable electroactive materials. The target compounds were obtained in moderate to high yield via the cyclization of the corresponding diketones or hydroxyketones, using phosphorus pentasulfide or acidic conditions. The ketones 12 and 17 were prepared directly from their hydroxy precursors by treatment with MnO2. The trans configuration of diketone 20 was confirmed by X-ray crystallography.

  DOI：

  10.1021/jo990198+

文献信息

• Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives
  作者：Filipe Vilela、Peter J Skabara、Christopher R Mason、Thomas D J Westgate、Asun Luquin、Simon J Coles、Michael B Hursthouse

  DOI：10.3762/bjoc.6.113

  日期：——

  We present a series of compounds by exploiting the unusual 1,4-aryl shift observed for electron-rich 1,3-dithiole-2-thione and tetrathiafulvalene (TTF) derivatives in the presence of perchloric acid. The mechanistic features of this rearrangement are discussed since this synthetic strategy provides an alternative route for the synthesis and functionalisation of sulfur rich compounds including redox active compounds of TTFs, and a Ni dithiolene.

  我们通过利用在高氯酸存在下观察到的富电子1,3-二硫代二唐和四硫富瓦烯（TTF）衍生物的不寻常的1,4-芳基转移，提出了一系列化合物。讨论了这种重排的机制特征，因为这种合成策略为合成和功能化硫富化合物提供了一条替代途径，包括TTF的氧化还原活性化合物和Ni二硫代烯。
• The acid-catalysed rearrangements of 4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione
  作者：Igor M. Serebryakov、Peter J. Skabara、Igor F. Perepichka

  DOI：10.1039/a901178a

  日期：——

  Under strongly acidic conditions, the title compound 1 readily participates in several possible rearrangement pathways, affording a product distribution which is relative to the choice of solvent and acid catalyst. Thus, using chloroform or acetone as the solvents and HBr or HClO4 as the catalysts, compounds 2–4 have been isolated and fully characterised; in addition, compound 5 was identified in the reaction mixture and characterised by 1H NMR spectroscopy. The reaction kinetics of the transformations have been studied by 1H NMR spectroscopy, using deuterated chloroform or acetone as the NMR solvents. A key intermediate in the reaction mechanisms is the allylic carbocation 6, which rearranges to give the fused system 3; in the presence of bromide anions, the carbocation forms an ion-pair intermediate 7, leading to the formation of compounds 2, 4 and/or 5, depending on the solvent.