2-[[4-ethylsulfanyl-2-[4-ethylsulfanyl-5-[2-(4-methylphenyl)sulfonyloxyethylsulfanyl]-1,3-thiaselenol-2-ylidene]-1,3-thiaselenol-5-yl]sulfanyl]ethyl 4-methylbenzenesulfonate | 444603-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[[4-ethylsulfanyl-2-[4-ethylsulfanyl-5-[2-(4-methylphenyl)sulfonyloxyethylsulfanyl]-1,3-thiaselenol-2-ylidene]-1,3-thiaselenol-5-yl]sulfanyl]ethyl 4-methylbenzenesulfonate
• CAS: 444603-68-3
• 化学式: C₂₈H₃₂O₆S₈Se₂
• 分子量: 879.006
• InChiKey: MVQAJTSZXULJLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-[[4-ethylsulfanyl-2-[4-ethylsulfanyl-5-[2-(4-methylphenyl)sulfonyloxyethylsulfanyl]-1,3-thiaselenol-2-ylidene]-1,3-thiaselenol-5-yl]sulfanyl]ethyl 4-methylbenzenesulfonate 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以82%的产率得到(2E)-2-(5,6-dihydro-[1,3]thiaselenolo[4,5-b][1,4]dithiin-2-ylidene)-5,6-dihydro-[1,3]thiaselenolo[4,5-b][1,4]dithiine
  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-ethylthio-5-[2-(tetrahydropyran-2-yloxy)ethylthio]-1,3-thiaselenole-2-one 在 盐酸 、 三乙胺 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 37.0h， 生成 2-[[4-ethylsulfanyl-2-[4-ethylsulfanyl-5-[2-(4-methylphenyl)sulfonyloxyethylsulfanyl]-1,3-thiaselenol-2-ylidene]-1,3-thiaselenol-5-yl]sulfanyl]ethyl 4-methylbenzenesulfonate
  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