4,5-Bis-(2,5-dimethyl-thiophen-3-yl)-[1,3]dithiol-2-one | 252264-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4,5-Bis-(2,5-dimethyl-thiophen-3-yl)-[1,3]dithiol-2-one
• 英文别名: 4,5-Bis(2,5-dimethylthiophen-3-yl)-1,3-dithiol-2-one
• CAS: 252264-80-5
• 化学式: C₁₅H₁₄OS₄
• 分子量: 338.54
• InChiKey: PURJUQKDRGNVQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±60.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-Bis-(2,5-dimethyl-thiophen-3-yl)-[1,3]dithiol-2-one 在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 以96%的产率得到4,5-bis(2,5-dimethylthien-3-yl)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Synthesis and Photochromic Properties of Functional Diarylethenes with a [1,3]dithiol-2-one (Thione) Bridging Unit

  摘要：

  In designing new photochromic compounds for optical data storage and photo-switching devices, the synthesis of a series of 4,5-diaryl-1,3-dithiol-2-one and 4,5-diaryl-1,3-dithiol-2-thione, which are suitable building blocks for incorporation with fluorophore, is herein reported. Our strategy needs the preliminary preparation of diarylalkynes, obtained by successive Sonogashira-Hagihara coupling-reactions in good yields (63-92%). A combination of these synthetic precursors with diisopropylxanthogen disulfide leads to the corresponding 4,5-diaryl-1,3-dithiol-2-ones under radical conditions with excellent yields (54-70%). The thionation of these compounds is obtained nearly quantitatively with phosphorous pentasulfide.

  DOI：

  10.1080/15421400590946451
• 作为产物：
  描述：

  3-碘-2,5-二甲基噻吩 在 copper(l) iodide sodium hydroxide 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 苄基三乙基氯化铵 作用下， 以 甲苯 、 苯 为溶剂， 反应 20.0h， 生成 4,5-Bis-(2,5-dimethyl-thiophen-3-yl)-[1,3]dithiol-2-one
  参考文献：
  名称：

  Synthesis and Photochromic Properties of Functional Diarylethenes with a [1,3]dithiol-2-one (Thione) Bridging Unit

  摘要：

  In designing new photochromic compounds for optical data storage and photo-switching devices, the synthesis of a series of 4,5-diaryl-1,3-dithiol-2-one and 4,5-diaryl-1,3-dithiol-2-thione, which are suitable building blocks for incorporation with fluorophore, is herein reported. Our strategy needs the preliminary preparation of diarylalkynes, obtained by successive Sonogashira-Hagihara coupling-reactions in good yields (63-92%). A combination of these synthetic precursors with diisopropylxanthogen disulfide leads to the corresponding 4,5-diaryl-1,3-dithiol-2-ones under radical conditions with excellent yields (54-70%). The thionation of these compounds is obtained nearly quantitatively with phosphorous pentasulfide.

  DOI：

  10.1080/15421400590946451

文献信息

• Synthesis of Tetrathiafluvalene Derivatives with Photochromic Diarylethene Moieties
  作者：Kingo Uchida、Go Masuda、Yoshifumi Aoi、Koji Nakayama、Masahiro Irie

  DOI：10.1246/cl.1999.1071

  日期：1999.10

  Tetrathiafulvalene (TTF) derivatives with diarylethene moieties have been synthesized. A derivative having 2,4,5-trimethylthiophene rings as the aryl groups showed photochromism, while a derivative with 2,5-dimethylthiophene rings did not show any color change by UV irradiation. The different reactivity was ascribed to the difference in the conformation of thiophene rings in the two derivatives.

  合成了带有二芳烯部分的四硫富瓦烯（TTF）衍生物。含有2,4,5-三甲基噻吩环作为芳基的衍生物显示出光致变色，而含有2,5-二甲基噻吩环的衍生物在紫外线照射下没有任何颜色变化。不同的反应性归因于这两种衍生物中噻吩环构象的差异。