4-ethylseleno-5-[2-(tetrahydropyran-2-yloxy)ethylthio]-1,3-thiaselenole-2-selone | 444603-47-8

• 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-ethylseleno-5-[2-(tetrahydropyran-2-yloxy)ethylthio]-1,3-thiaselenole-2-selone
• 英文别名: 5-Ethylselanyl-4-[2-(oxan-2-yloxy)ethylsulfanyl]-1,3-thiaselenole-2-selone
• CAS: 444603-47-8
• 化学式: C₁₂H₁₈O₂S₂Se₃
• 分子量: 495.286
• InChiKey: LCQQFIMUDAPBSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethylseleno-5-[2-(tetrahydropyran-2-yloxy)ethylthio]-1,3-thiaselenole-2-selone 在 三甲氧基磷 作用下， 以 苯 为溶剂， 反应 1.0h， 以67%的产率得到2-[2-[[4-ethylselanyl-2-[4-ethylselanyl-5-[2-(oxan-2-yloxy)ethylsulfanyl]-1,3-thiaselenol-2-ylidene]-1,3-thiaselenol-5-yl]sulfanyl]ethoxy]oxane
  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：

  2-(四氢-2H-吡喃-2-基氧基)乙基硫氰酸酯 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-ethylseleno-5-[2-(tetrahydropyran-2-yloxy)ethylthio]-1,3-thiaselenole-2-selone
  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