4,5-bis(5-chloropentylsulfanyl)-1,3-dithiole-2-thione | 193148-62-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-bis(5-chloropentylsulfanyl)-1,3-dithiole-2-thione
• CAS: 193148-62-8
• 化学式: C₁₃H₂₀Cl₂S₅
• 分子量: 407.538
• InChiKey: OXIBESDECMWMBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-bis(5-chloropentylsulfanyl)-1,3-dithiole-2-thione 在 sodium iodide 、 亚磷酸三乙酯 作用下， 以 丁酮 、 xylene 为溶剂， 反应 22.0h， 生成 9-[4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-ylidene]-10-[4,5-bis(5-iodopentylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene
  参考文献：
  名称：

  π-扩展四硫富瓦烯中的极端构象约束：双桥和三桥环芳烃的异常拓扑和氧化还原行为

  摘要：

  已经合成了双桥和三桥 9,10-双 (1,3-二硫醇-2-亚基)-9,10-二氢蒽 (ex-TTF) 衍生物。关键步骤是 ex-TTF-dithiolate 试剂的生成和大环化反应。双桥环芳烃 15 和 16 以及三桥系统 23 的 X 射线晶体结构表明，二硫醇环之间的短桥增强了 ex-TTF 骨架的鞍状构象。与之前所有的 ex-TTF 衍生物（显示单个准可逆的双电子氧化波，D0 --> D2+）不同，环芳烃的循环伏安法显示了两个可逆的单电子氧化步骤（D0 --> D*+ --> D2+)，半波电位 (E2(1/2) - E1(1/2)) 之间的差异为 0.22-0.26 V。在不受限制的 ex-TTF 系统（包括单桥环芳烃）中驱动第二个氧化过程的构象变化和芳香性的增加已被多重桥接阻止。自由基阳离子物种产生了一个非常宽的低能带（λmax = 2175 和 2040 nm，分别为 15 和

  DOI：

  10.1021/ja062358m
• 作为产物：
  描述：

  1-溴-5-氯戊烷 、 bis(tetrabutylammonium) bis(2-thioxo-1,3-dithiole-4,5-dithiolato)zincate 以 丙酮 为溶剂， 反应 48.0h， 以96%的产率得到4,5-bis(5-chloropentylsulfanyl)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes

  摘要：

  A series of novel tetrathiafulvalenophanes has been synthesized, in which two tetrathiafulvalenes (TTF) are linked in a crisscross-overlapped arrangement by four alkylenedithio bridges. Their molecular structures were elucidated by X-ray crystal analyses, being characterized by the bent TTF skeletons as well as the unique stacking mode. The degree of the bend largely depends on both the length and conformational rigidity of the alkylenedithio chains. The short and rigid chains induce severe bending, which brings about a hypsochromical effect in the electronic absorption spectra. On the other hand, the long and flexible chains reduce the strain and make an inside cavity large enough to include a guest molecule. In addition, the less strained compounds can effect an intramolecular transannular Coulombic interaction between their two TTF units in solution, as demonstrated by multistage redox waves in the cyclic voltammograms. All the radical cation salts formed from these tetrathiafulvalenophanes have conductivities of the same order of 10(-6)-10(-7) S cm(-1), which are apparently independent of the donor and the counterion species.

  DOI：

  10.1021/jo962239x