4-ethylseleno-5-(2-hydroxyethylseleno)-1,3-dithiole-2-thione | 444603-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4-ethylseleno-5-(2-hydroxyethylseleno)-1,3-dithiole-2-thione
• 英文别名: 4-Ethylselanyl-5-(2-hydroxyethylselanyl)-1,3-dithiole-2-thione
• CAS: 444603-51-4
• 化学式: C₇H₁₀OS₃Se₂
• 分子量: 364.274
• InChiKey: POVIEGYWMDIFJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethylseleno-5-(2-hydroxyethylseleno)-1,3-dithiole-2-thione 在 三溴化磷 、 sodium iodide 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 5.0h， 生成 4-ethylseleno-1,3-dithiole-2-thione
  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
• 作为产物：
  描述：

  4-ethylseleno-5-[2-(tetrahydropyran-2-yloxy)ethylseleno]-1,3-dithiole-2-thine 在 盐酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.0h， 以81%的产率得到4-ethylseleno-5-(2-hydroxyethylseleno)-1,3-dithiole-2-thione
  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