bis(4-methylthiophen-3-yl)sulfide | 379692-12-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis(4-methylthiophen-3-yl)sulfide
• 英文别名: 3-Methyl-4-(4-methylthiophen-3-yl)sulfanylthiophene
• CAS: 379692-12-3
• 化学式: C₁₀H₁₀S₃
• 分子量: 226.387
• InChiKey: ASPDNZSGTONNFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(4-methylthiophen-3-yl)sulfide 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 28.0h， 生成 2-bromo-3,5-dimethyl-6-phenyl-dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide
  参考文献：
  名称：

  Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

  摘要：

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

  DOI：

  10.1021/ja2065522
• 作为产物：
  描述：

  3-溴-4-甲基噻吩 在 四(三苯基膦)钯 、 双(三丁基锡)硫醚 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到bis(4-methylthiophen-3-yl)sulfide
  参考文献：
  名称：

  Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

  摘要：

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

  DOI：

  10.1021/ja2065522

文献信息

• Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils
  作者：Ilaria Palamà、Francesca Di Maria、Ilenia Viola、Eduardo Fabiano、Giuseppe Gigli、Cristian Bettini、Giovanna Barbarella

  DOI：10.1021/ja2065522

  日期：2011.11.9

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.