2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-4-methyl-5-methylsulfanyl-[1,3]dithiole | 163226-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-4-methyl-5-methylsulfanyl-[1,3]dithiole
• 英文别名: (2E)-2-[(4-methoxyphenyl)methylidene]-4-methyl-5-methylsulfanyl-1,3-dithiole
• CAS: 163226-70-8
• 化学式: C₁₃H₁₄OS₃
• 分子量: 282.452
• InChiKey: KHPHOAXQWYYNGQ-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-4-methyl-5-methylsulfanyl-[1,3]dithiole 以 乙腈 为溶剂， 以71%的产率得到(2Z)-2-[(2Z)-1,2-bis(4-methoxyphenyl)-2-(4-methyl-5-methylsulfanyl-1,3-dithiol-2-ylidene)ethylidene]-4-methyl-5-methylsulfanyl-1,3-dithiole
  参考文献：
  名称：

  Electrochemical Synthesis of Extended TTF

  摘要：

  An efficient electrochemical synthesis of new extended TTFs (tetrathiafulvalenes) starting from 1,4-dithiafulvenes is presented, and the mechanism is discussed. Single crystal X-ray structure of the neutral extended TTF 7d is reported. These novel pi-electron donor molecules show one two-electron reversible oxidation wave in cyclic voltammetry.

  DOI：

  10.1021/jo00113a026
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 2-Diethoxyphosphoryl-4-methyl-5-methylsulfanyl-1,3-dithiole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-4-methyl-5-methylsulfanyl-[1,3]dithiole
  参考文献：
  名称：

  Electrochemical Synthesis of Extended TTF

  摘要：

  An efficient electrochemical synthesis of new extended TTFs (tetrathiafulvalenes) starting from 1,4-dithiafulvenes is presented, and the mechanism is discussed. Single crystal X-ray structure of the neutral extended TTF 7d is reported. These novel pi-electron donor molecules show one two-electron reversible oxidation wave in cyclic voltammetry.

  DOI：

  10.1021/jo00113a026

文献信息

• Mechanism of Dimerization of 1,4-Dithiafulvenes into TTF Vinylogues
  作者：Philippe Hapiot、Dominique Lorcy、André Tallec、Roger Carlier、Albert Robert

  DOI：10.1021/jp961048v

  日期：1996.1.1

  Mechanism of the oxidative dimerization of DTF (dithiafulvenes) to form TTF vinylogues (tetrathiafulvalenes) has been investigated by cyclic voltammetry at low and high scan rates for a series of substituted DTF. It involves first the formation of the cation radical which couples to form the protonated dication. This dication slowly deprotonates to give the final TTF (k = 0.5−1 s-1). The dimerization

  已通过循环伏安法在低和高扫描速率下对一系列取代的DTF进行了DTF（二硫​​富富烯）氧化二聚形成TTF乙烯基（四硫富瓦烯）的机理的研究。它首先涉及阳离子自由基的形成，该阳离子自由基结合形成质子化的指示。该指示缓慢地去质子化，得到最终的TTF（k = 0.5-1 s -1）。发现二聚化速率常数在k dim＝（2-4）×10 8 L mol -1 s -1的范围内，并且随取代基的性质变化不大。
• 1,2-Bis(5-methyl-4-methylthio-1,3-dithiolium-2-ylidene)-1,2-diphenylethane Bis(triiodide) and 1,2-Bis(4-methoxyphenyl)-1,2-bis(5-methyl-4-methylthio-1,3-dithiolium-2-ylidene)ethane Diperchlorate
  作者：C. Rimbaud、P. Le Magueres、L. Ouahab、D. Lorcy、A. Robert

  DOI：10.1107/s010827019701768x

  日期：1998.5.15

  The non-planar organic donor 1,2-diaryl-1,2-bis(5-methyl-4-methylthio-1,3-dithiol-2-ylidene)ethane forms dication charge-transfer salts with iodine, C24H22S62+.2I(3)(-), and with perchlorate, C26H26O2S62+.2ClO(4)(-). In the former salt, mixed stacks of triiodide and dications are observed, while separated organic and inorganic columns are found in the perchlorate salt.