meso-4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione | 245495-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: meso-4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione
• 英文别名: 5-[(R)-hydroxy(thiophen-2-yl)methyl]-4-[(S)-hydroxy(thiophen-2-yl)methyl]-1,3-dithiole-2-thione
• CAS: 245495-07-2
• 化学式: C₁₃H₁₀O₂S₅
• 分子量: 358.551
• InChiKey: PYFUQIWHZQVIAO-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  meso-4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以100%的产率得到[5-(thiophene-2-carbonyl)-2-thioxo-[1,3]dithiol-4-yl]thiophen-2-yl-methanone
  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：

  三硫代碳酸亚乙烯酯 、 2-噻吩甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以67%的产率得到dl-4,5-bis(2-thienylhydroxymethyl)-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+