pyrazine-2,3-trithiocarbonate | 4442-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: pyrazine-2,3-trithiocarbonate
• 英文别名: Pyrazinotrithiocarbonate；pyrazino-2,3-dithiole-2-thione；pyrazine-1,3-dithiole-2-thione；[1,3]Dithiolo[4,5-b]pyrazine-2-thione
• CAS: 4442-36-8
• 化学式: C₅H₂N₂S₃
• 分子量: 186.282
• InChiKey: KUQKCWMPGBTVOY-UHFFFAOYSA-N

物化性质

• 沸点：
  396.9±45.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  pyrazine-2,3-trithiocarbonate 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以69%的产率得到[1,3]dithiolo[4,5-b]pyrazine-2-one
  参考文献：
  名称：

  Extended TTF-type donors fused with pyrazine units; synthesis and characterization

  摘要：

  Pyrazinedicyanoethylthiotetrathiafulvalene, (pzdc-TTF) (1a), an extended TIFF fused with a pyrazine moiety and also a dithiolene ligand precursor, was synthesized through a cross-coupling with triethyl phosphite between pyrazine-1,3-dithiole-2-thione (I) and 4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-one (III). This reaction also yields to dipyrazine TIFF derivative (1b) and 2,3,6,7-Tetrakis(2-cyanoethylthio)TTF (1c), resulting from the self-coupling reactions of the thione (I) and ketone (III). The crystal structure of 1a is composed by pairs of head to head donor stacks of pzdc-TTF molecules along b in opposite orientations. Single crystals of 1b revealed a new polymorph with a face-to-face pi-stacking motif. The electrochemical properties of 1a studied by cyclic voltammetry (CV) in DMF, shows two single electron oxidation processes typical of TTF-based donors; one pair of asymmetric redox waves centered at 627 mV versus Ag/Ag+ is ascribed to the couple [pzdc-TTF](+)/[pzdc-TTF](2+), and one pair of quasi-reversible redox waves centered at 430 mV is ascribed to the couple [pzdc-TTF](0)/[pzdc-TTF](+). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.131
• 作为产物：
  描述：

  2,3-二氯吡嗪 、 potassium trithiocarbonate 反应 48.0h， 以1.268 g的产率得到pyrazine-2,3-trithiocarbonate
  参考文献：
  名称：

  Extended TTF-type donors fused with pyrazine units; synthesis and characterization

  摘要：

  Pyrazinedicyanoethylthiotetrathiafulvalene, (pzdc-TTF) (1a), an extended TIFF fused with a pyrazine moiety and also a dithiolene ligand precursor, was synthesized through a cross-coupling with triethyl phosphite between pyrazine-1,3-dithiole-2-thione (I) and 4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-one (III). This reaction also yields to dipyrazine TIFF derivative (1b) and 2,3,6,7-Tetrakis(2-cyanoethylthio)TTF (1c), resulting from the self-coupling reactions of the thione (I) and ketone (III). The crystal structure of 1a is composed by pairs of head to head donor stacks of pzdc-TTF molecules along b in opposite orientations. Single crystals of 1b revealed a new polymorph with a face-to-face pi-stacking motif. The electrochemical properties of 1a studied by cyclic voltammetry (CV) in DMF, shows two single electron oxidation processes typical of TTF-based donors; one pair of asymmetric redox waves centered at 627 mV versus Ag/Ag+ is ascribed to the couple [pzdc-TTF](+)/[pzdc-TTF](2+), and one pair of quasi-reversible redox waves centered at 430 mV is ascribed to the couple [pzdc-TTF](0)/[pzdc-TTF](+). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.131

文献信息

• Synthesis and properties of hetero-halogenated TTFsElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/ob/b3/b310822h/
  作者：Rie Suizu、Tatsuro Imakubo

  DOI：10.1039/b310822h

  日期：——

  Novel hetero-halogenated TTFs containing both chlorine and iodine atoms were prepared and their unique characters based on the halogen atoms were examined.

  制备了新型含有氯和碘原子的异卤化TTFs，并对其基于卤素原子的独特特性进行了研究。
• Pyrazinoethylenedithiotetrathiafulvalene: a new unsymmetrical π-donor
  作者：G. C. Papavassiliou、S. Y. Yiannopoulos、J. S. Zambounis

  DOI：10.1039/c39860000820

  日期：——

  synthesized from pyrazinotrithiocarbonate and 4,5-ethylenedithio-1,3-dithiole-2-thione via triethyl phosphite cross coupling, has been characterized and several charge-transfer complexes of this new π-donor have been prepared.

  表征了由吡嗪基三硫代碳酸酯和4，5-亚乙基二硫代-1,3-二硫代-2-硫酮通过亚磷酸三乙酯交叉偶联合成的标题化合物，并制备了该新的π-给体的几种电荷转移配合物。
• New π -Donor Molecules with a Pyrazino Group and their Conducting Salts
  作者：G. C. Papavassiliou、Yohji Misaki、Kazuko Takahashi、Jun-ichi Yamada、G. A. Mousdis、Takashi Sharahata、Toshihiro Ise

  DOI：10.1515/znb-2001-0313

  日期：2001.3.1

  The preparation and characterization of some π-donors with a pyrazine-edge-group as well as with tetrathiapentalene-, thiophene-, and dihydrobenzoselenophene-spacer-groups are de­ scribed. Some of these donors give conducting charge transfer complexes with TCNQ and/or cation radical salts with I₃ ^-, BF₄ ^-and PF₆ ^-as counter anions.

  摘要：本文描述了一些具有吡嗪边基团、四硫代戊二烯、噻吩和二氢苯并硒的空穴传输分子的制备和表征。其中一些给出与TCNQ形成导电的电荷转移复合物，或与I₃ ^-、BF₄ ^-和PF₆ ^-等阳离子盐形成的阳离子基盐。
• Solvent dependence of crystal morphology, donor/anion ratio and electrical conductivity in a series of hexagonal supramolecular organic conductors based on diiodo(pyrazino)tetrathiafulvalene (DIP)
  作者：Tatsuro Imakubo、Ryosuke Murayama

  DOI：10.1039/c2ce26739j

  日期：——

  A series of hexagonal supramolecular organic conductors has been tailored by the iodine bond based on the selenium-free π-donor and halogen-free solvent. The solvent dependence of crystal morphology, donor/anion ratio and electrical conductivity was investigated together with characteristic recyclability of the neutral donor molecule.

  基于不含硒的π供体和不含卤素的溶剂，通过碘键定制了一系列六角形的超分子有机导体。研究了溶剂对晶体形态，供体/阴离子比和电导率的依赖性以及中性供体分子的可回收性。
• Pyrazino-methyl-ethylenedithio- tetrathiafulvalene, Precursor o τ-Phase Conductors
  作者：G. C. Papavassiliou、A. Terzis、C. P. Raptopoulou

  DOI：10.1515/znb-2001-0916

  日期：2001.9.1

  Modifications of the previously reported meth­ods of preparation of racemic pyrazino-methyl-ethylenedithio-tetrathiafulvalene, i.e., 2-(5,6-dihy-dro-5-methyl-1,3-dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiolo[4,5-b]pyrazine, and their cat­ ion radical salts with linear counter anions are re­ ported. ESR spectra and preliminary X-ray dif­ fraction measurements indicate that the salts crystallize in the τ-phase (tetragonal system).

  报道了制备外消旋吡嗪基甲基乙烯二硫富瓦烯的先前报告方法的改进，即2-（5,6-二氢-5-甲基-1,3-二硫杂环[4,5-b][1,4]二硫烯-2-基）-1,3-二硫杂环[4,5-b]吡嗪及其与线性对离子反应得到的阳离子自由基盐。ESR光谱和初步的X射线衍射测量表明，盐结晶于τ相（四方晶系）。