4,5-Bis-(2-chloro-ethylsulfanyl)-[1,3]dithiole-2-thione | 138682-23-2

• 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-(2-chloro-ethylsulfanyl)-[1,3]dithiole-2-thione
• 英文别名: 4,5-Bis(2-chloroethylsulfanyl)-1,3-dithiole-2-thione
• CAS: 138682-23-2
• 化学式: C₇H₈Cl₂S₅
• mdl: MFCD11655896
• 分子量: 323.377
• InChiKey: HLRXHTBVKQNVPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 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-(2-chloro-ethylsulfanyl)-[1,3]dithiole-2-thione 在 mercury(II) diacetate 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 2.0h， 以94%的产率得到6-喹喔啉丙酸,-α--氨基-(9CI)
  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
• 作为产物：
  描述：

  1-(肉豆蔻酰<十四酰>)-2-(7,7-二氟肉豆蔻酰<十四酰>)甘油-3-二氧磷基胆碱 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到4,5-Bis-(2-chloro-ethylsulfanyl)-[1,3]dithiole-2-thione
  参考文献：
  名称：

  高功能化四硫富瓦烯（TTF）衍生物

  摘要：

  描述了一系列新型官能化的四硫富瓦烯给体的有效合成方法，特别是被乙烯基硫基和丙烯酸酯基取代的那些。循环伏安法研究了溶液的氧化还原特性。

  DOI：

  10.1039/c39910001638

文献信息

• Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF)
  作者：Adrian J. Moore、Martin R. Bryce、Graeme Cooke、Gary J. Marshallsay、Peter J. Skabara、Andrei S. Batsanov、Judith A. K. Howard、Stephen T. A. K. Daley

  DOI：10.1039/p19930001403

  日期：——

  particularly versatile building block for the synthesis of a range of new mono-functionalised TTF derivatives containing ether, ester, acrylate, urethane and vinylthio groups in the side chain. Onepot syntheses of ethylenedithio-TTF (EDT-TTF) and ethylenediseleno-TTF (EDS-TTF) from TTF are reported. The structure of EDS-TTF has been determined by single crystal X-ray analysis which reveals dimers with molecular

  单硅化四硫富瓦烯（TTF）与元素硫或元素硒在–78°C的反应产生瞬态物质TTF-S – Li +和TTF-Se – Li +分别被一系列烷基卤捕获，得到了新的烷基硫代和烷基硒代TTF衍生物。TTF-硫醇盐阴离子与2-溴乙醇的反应生成4-（2-羟乙基硫基）四硫富瓦烯，它是用于合成一系列新的含醚，酯，丙烯酸酯，氨基甲酸酯和乙烯基硫基的新型单官能化TTF衍生物的通用型结构单元侧链中的基团。据报道，由TTF一锅合成乙二硫基-TTF（EDT-TTF）和乙二硒基-TTF（EDS-TTF）。EDS-TTF的结构已通过单晶X射线分析确定，该分析揭示了分子平面彼此正交的二聚体。
• Highly-functionalised tetrathiafulvalene (TTF) derivatives
  作者：Adrian J. Moore、Martin R. Bryce

  DOI：10.1039/c39910001638

  日期：——

  Efficient syntheses are described for a range of new functionalised tetrathiafulvalene donors, notably those substituted with vinylthio and acrylate groups; solution redox properties have been studied by cyclic voltammetry.

  描述了一系列新型官能化的四硫富瓦烯给体的有效合成方法，特别是被乙烯基硫基和丙烯酸酯基取代的那些。循环伏安法研究了溶液的氧化还原特性。
• Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes
  作者：Kazuo Takimiya、Koichi Imamura、Youji Shibata、Yoshio Aso、Fumio Ogura、Tetsuo Otsubo

  DOI：10.1021/jo962239x

  日期：1997.8.1

  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.