(Z)-5,5'-Bis-[2-(2-iodo-ethoxy)-ethylsulfanyl]-4,4'-bis-methylsulfanyl-[2,2']bi[[1,3]dithiolylidene] | 222023-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: (Z)-5,5'-Bis-[2-(2-iodo-ethoxy)-ethylsulfanyl]-4,4'-bis-methylsulfanyl-[2,2']bi[[1,3]dithiolylidene]
• 英文别名: 4-[2-(2-iodoethoxy)ethylsulfanyl]-2-[4-[2-(2-iodoethoxy)ethylsulfanyl]-5-methylsulfanyl-1,3-dithiol-2-ylidene]-5-methylsulfanyl-1,3-dithiole
• CAS: 222023-00-9
• 化学式: C₁₆H₂₂I₂O₂S₈
• 分子量: 756.686
• InChiKey: QHFGBQIKTSWAMT-UHFFFAOYSA-N

物化性质

• 沸点：
  602.8±55.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (Z)-5,5'-Bis-[2-(2-iodo-ethoxy)-ethylsulfanyl]-4,4'-bis-methylsulfanyl-[2,2']bi[[1,3]dithiolylidene] 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,7(6)-bis[2-(2-aminoethoxy)ethylthio]-2,7(6)-bis(methylthio)tetrathiafulvalene
  参考文献：
  名称：

  Donor−Acceptor Macrocycles Incorporating Tetrathiafulvalene and Pyromellitic Diimide: Syntheses and Crystal Structures

  摘要：

  DOI：

  10.1002/1099-0690(200006)2000:11<2135::aid-ejoc2135>3.0.co;2-p
• 作为产物：
  描述：

  (Z)-5,5'-Bis-[2-(2-chloro-ethoxy)-ethylsulfanyl]-4,4'-bis-methylsulfanyl-[2,2']bi[[1,3]dithiolylidene] 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以86%的产率得到(Z)-5,5'-Bis-[2-(2-iodo-ethoxy)-ethylsulfanyl]-4,4'-bis-methylsulfanyl-[2,2']bi[[1,3]dithiolylidene]
  参考文献：
  名称：

  Stable Macrocyclic and Tethered Donor−Acceptor Systems. Intramolecular Bipyridinium and Tetrathiafulvalene Assemblies

  摘要：

  A series of compounds has been prepared in which a tetrathiafulvalene (TTF)-derived donor is covalently tethered or bridged to one or more bipyridinium (viologen) accepters. The relative degree of charge transfer observed in this series is discussed as a function of structure. The greatest CT effect is seen in the cyclophanes 9a-c and 13.

  DOI：

  10.1021/jo961782a

文献信息

• Tetrathiafulvalene Thiolates: Important Synthetic Building Blocks for Macrocyclic and Supramolecular Chemistry
  作者：Klaus Simonsen、Jan Becher

  DOI：10.1055/s-1997-1001

  日期：1997.11

  The Preparation of rather complex molecular assemblies can now be accomplished by using a complete set of tetrathiafulvalene (TTF) based building blocks. The facile deprotection of the 2-cyanoethyl group, a versatile protecting group for 1,3-dithiolium-2-thione-4,5-dithiolaes and TTF-thiolates have proven to be a viable method for the incorporation of TTF units into macrocyclic and supramolecular compounds. Especially the stepwise protection-deprotection methodology have been used extensively by our group for the preparation of two and three dimensional macrocyclic (mono-, bis- and tricyclic) as well as TTF-based supramolecular systems. The generation, utilization and scope of the generated thiolates are illustrated by several examples: Dendrimeric and oligo-TTF's, three dimensional tetrathafulvalenophanes, TTF-containing catenanes and rotaxanes and donor acceptor systems based on TTF as the donating portion.

  现在，通过使用一整套基于四噻吩（TTF）的构建模块，可以制备相当复杂的分子组装体。2-Cyanoethyl 基团是 1,3-二硫代-2-硫酮-4,5-二硫环戊烯和 TTF-硫代酸酯的通用保护基团，对该基团进行简易脱保护已被证明是将 TTF 单元加入大环和超分子化合物的可行方法。特别是分步保护-保护方法已被我们小组广泛用于制备二维和三维大环（单环、双环和三环）以及基于 TTF 的超分子体系。我们通过几个实例来说明所生成的硫代化合物的生成、利用和应用范围：树枝状和低聚 TTF、三维四富戊烯烷、含 TTF 的卡替烷和轮烷以及以 TTF 为捐献部分的捐献受体系统。