1-Aza-2,3-dichlorothianthrene | 158696-59-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Aza-2,3-dichlorothianthrene
• 英文别名: 2,3-Dichloro-[1,4]benzodithiino[3,2-b]pyridine
• CAS: 158696-59-4
• 化学式: C₁₁H₅Cl₂NS₂
• 分子量: 286.205
• InChiKey: BEIOFNLZOUMXST-UHFFFAOYSA-N

物化性质

• 沸点：
  425.9±45.0 °C(predicted)
• 密度：
  1.571±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Aza-2,3-dichlorothianthrene 在 碳酸氢钠 、 thallium(III) trifluoroacetate 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 6.5h， 生成 6-aza-5,7,12,14-tetrathiapentacene
  参考文献：
  名称：

  Synthesis, Properties, and X-ray Structure of 6-Aza-5,7,12,14-tetrathiapentacene as a Novel Polyheterocyclic Electron Donor, and Related Compounds

  摘要：

  Two new compounds, 1-aza-2,3-dichlorothianthrene (5) and 6-aza-5,7,12,14-tetrathiapentacene (6) have been prepared by reaction of 2,3,5,6-tetrachloropyridine (4) and 1,2-benzenedithiol in dimethylformamide (DMF) in the presence of sodium bicarbonate. On the other hand, the synthesis of two known compounds, 1-azathianthrene (7) and 5,7,12,14-tetrathiapentacene (8) have been improved by using the same synthetic procedure as above, starting from 2,3-dichloropyridine and 1,2,4,5-tetrachlorobenzene, respectively. The radical cations of 6-8 have been generated in fluid solution and they are stable enough to be analyzed by electron paramagnetic resonance (EPR). The hyperfine coupling (hfc) constants in the EPR spectra have been assigned according with those from thianthrene radical cation (10), reported in the literature, and with semiempirical estimations (McLachlan method). The cyclic voltammogram of 6 exhibits a redox couple (E degrees = 1.07 V vs SCE) which is attributed to the oxidation to its radical cation 6(.+), and a second irreversible peak (E(p)(a) = 1.25 V) which is ascribed to the formation of the unstable dication 6(2+). X-ray structure of 6 shows that the molecule has a stable chair-shaped conformation with an interplanar angle between benzenes and pyridine ring of 134.7(1)degrees. The crystal packing presents a stacking pattern and the molecules overlap showing diagonal shifts in the stack.

  DOI：

  10.1021/jo00100a022
• 作为产物：
  描述：

  1,2-苯二硫醇 以66%的产率得到
  参考文献：
  名称：

  Marti Cristina, Irurre Jose, Alvarez-Larena Angel, Piniella Joan F., Bril+, J. Org. Chem, 59 (1994) N 21, S 6200-6207

  摘要：

  DOI：

文献信息

• Marti Cristina, Irurre Jose, Alvarez-Larena Angel, Piniella Joan F., Bril+, J. Org. Chem, 59 (1994) N 21, S 6200-6207
  作者：Marti Cristina, Irurre Jose, Alvarez-Larena Angel, Piniella Joan F., Bril+

  DOI：——

  日期：——
• Synthesis, Properties, and X-ray Structure of 6-Aza-5,7,12,14-tetrathiapentacene as a Novel Polyheterocyclic Electron Donor, and Related Compounds
  作者：Cristina Marti、Jose Irurre、Angel Alvarez-Larena、Joan F. Piniella、Enric Brillas、Lluis Fajari、Carlos Aleman、Luis Julia

  DOI：10.1021/jo00100a022

  日期：1994.10

  Two new compounds, 1-aza-2,3-dichlorothianthrene (5) and 6-aza-5,7,12,14-tetrathiapentacene (6) have been prepared by reaction of 2,3,5,6-tetrachloropyridine (4) and 1,2-benzenedithiol in dimethylformamide (DMF) in the presence of sodium bicarbonate. On the other hand, the synthesis of two known compounds, 1-azathianthrene (7) and 5,7,12,14-tetrathiapentacene (8) have been improved by using the same synthetic procedure as above, starting from 2,3-dichloropyridine and 1,2,4,5-tetrachlorobenzene, respectively. The radical cations of 6-8 have been generated in fluid solution and they are stable enough to be analyzed by electron paramagnetic resonance (EPR). The hyperfine coupling (hfc) constants in the EPR spectra have been assigned according with those from thianthrene radical cation (10), reported in the literature, and with semiempirical estimations (McLachlan method). The cyclic voltammogram of 6 exhibits a redox couple (E degrees = 1.07 V vs SCE) which is attributed to the oxidation to its radical cation 6(.+), and a second irreversible peak (E(p)(a) = 1.25 V) which is ascribed to the formation of the unstable dication 6(2+). X-ray structure of 6 shows that the molecule has a stable chair-shaped conformation with an interplanar angle between benzenes and pyridine ring of 134.7(1)degrees. The crystal packing presents a stacking pattern and the molecules overlap showing diagonal shifts in the stack.