4,5-Bis[(2'-tosylethyl)thio]-1,3-dithiole-2-thione | 141801-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-Bis[(2'-tosylethyl)thio]-1,3-dithiole-2-thione
• 英文别名: 2-[[5-[2-(4-Methylphenyl)sulfonyloxyethylsulfanyl]-2-sulfanylidene-1,3-dithiol-4-yl]sulfanyl]ethyl 4-methylbenzenesulfonate
• CAS: 141801-55-0
• 化学式: C₂₁H₂₂O₆S₇
• 分子量: 594.864
• InChiKey: RCPLDRAWQJUKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,5-Bis[(2'-tosylethyl)thio]-1,3-dithiole-2-thione 在 lithium bromide 、 N,N'-二甲基乙二胺 作用下， 以 丙酮 、 xylene 为溶剂， 反应 29.0h， 生成 <2,2'>-Bis-<1,3>dithiolanyliden
  参考文献：
  名称：

  Crown ether annelated tetrathiafulvalenes. 2

  摘要：

  A synthetic procedure leading to derivatives of tetrathiafulvalene (TTF) incorporating polyether chains of various lengths, some nitrogen analogs, and a 2,6-bis(methylene)pyridine analog has been developed. These compounds possess cage-type structures which were confirmed by X-ray crystallography in four cases, two of which are reported herein for the first time. Structural and electronic features of these cage molecules were correlated to oxidation potentials by the use of semiempirical methods (MNDO-PM3). An investigation of the alkali metal ion affinity using PDMS revealed that these compounds are poor ligands. Finally, in one case, protonation of the core TTF was studied by NMR.

  DOI：

  10.1021/jo00058a013
• 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 、 对甲苯磺酰氯 以 吡啶 为溶剂， 生成 4,5-Bis[(2'-tosylethyl)thio]-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

文献信息

• Crown ether annelated tetrathiafulvalenes. 2
  作者：T. K. Hansen、T. Joergensen、F. Jensen、P. H. Thygesen、K. Christiansen、M. B. Hursthouse、M. E. Harman、M. A. Malik、B. Girmay

  DOI：10.1021/jo00058a013

  日期：1993.3

  A synthetic procedure leading to derivatives of tetrathiafulvalene (TTF) incorporating polyether chains of various lengths, some nitrogen analogs, and a 2,6-bis(methylene)pyridine analog has been developed. These compounds possess cage-type structures which were confirmed by X-ray crystallography in four cases, two of which are reported herein for the first time. Structural and electronic features of these cage molecules were correlated to oxidation potentials by the use of semiempirical methods (MNDO-PM3). An investigation of the alkali metal ion affinity using PDMS revealed that these compounds are poor ligands. Finally, in one case, protonation of the core TTF was studied by NMR.
• 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.