4,5-ethylenedithio-1-selenole-3-thiole-2-one | 128346-57-6

• 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-ethylenedithio-1-selenole-3-thiole-2-one
• 英文别名: 5,6-dihydro-2-oxo-1,3-thiaselenolo[2,3-d][1,4]thiaselenin；5,6-Dihydro-[1,3]thiaselenolo[4,5-b][1,4]dithiin-2-one
• CAS: 128346-57-6
• 化学式: C₅H₄OS₃Se
• 分子量: 255.244
• InChiKey: HEXLBCNLNLVRTD-UHFFFAOYSA-N

物化性质

• 沸点：
  372.4±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-ethylenedithio-1-selenole-3-thiole-2-one 在 亚磷酸三乙酯 作用下， 反应 0.5h， 以5.2%的产率得到bis(ethylenedithio)diselenadithiafulvalene
  参考文献：
  名称：

  Lagouvardos, D. J.; Papavassiliou, G. C., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 6, p. 898 - 900

  摘要：

  DOI：
• 作为产物：
  描述：

  4-ethylthio-5-[2-(tetrahydropyran-2-yloxy)ethylthio]-1,3-thiaselenole-2-thione 在 吡啶 、 盐酸 、 mercury(II) diacetate 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 88.0h， 生成 4,5-ethylenedithio-1-selenole-3-thiole-2-one
  参考文献：
  名称：

  Synthetic Procedure for Various Selenium-Containing Electron Donors of the Bis(Ethylenedithio)tetrathiafulvalene (BEDT-TTF) Type

  摘要：

  Six selenium variants of BEDT-TTF have been successfully synthesized by a newly developed synthetic method that involves a combination of two key reactions for the construction of two kinds of heterocyclic rings: the first is a one-pot formation of 1,3-dichalcogenole-2-chalcogenones from a common starting material, THP-protected 2-(ethynylthio)ethanol, leading to the inner five-membered rings, and the other is the annelation of the outer six-membered heterocyclic ring onto the inner ring by an intramolecular transalkylation reaction on a chalcogen atom. This method turned out to be widely applicable to the syntheses of the electron donors of bis(ethylenedithio)- and bis(ethyleneselenothio)-substituted types. However, synthetic attempts to form analogous donors of the bis(ethylenediseleno)-substituted type from THP-protected 2-(ethynylseleno)ethanol were unsuccessful. This is attributable to the predominance of side-reactions via a seleniranium (episelenonium) salt over the desired six-membered ring formation by transalkylation via a seleninium salt.

  DOI：

  10.1021/jo016393h

文献信息

• Papavassiliou, G. C.; Kakoussis, V. C.; Lagouvardos, D. J., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 181, p. 171 - 184
  作者：Papavassiliou, G. C.、Kakoussis, V. C.、Lagouvardos, D. J.、Mousdis, G. A.

  DOI：——

  日期：——