Azuleno[1,2-d][1,3]dithiol-2-one | 1451059-78-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: Azuleno[1,2-d][1,3]dithiol-2-one
• 英文别名: azuleno[1,2-d][1,3]dithiol-2-one
• CAS: 1451059-78-1
• 化学式: C₁₁H₆OS₂
• 分子量: 218.3
• InChiKey: XUFWXVGQIOOLPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±28.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 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：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三硫代碳酸亚乙烯酯 、 Azuleno[1,2-d][1,3]dithiol-2-one 在 亚磷酸三乙酯 作用下， 以22%的产率得到2-(1,3-Dithiol-2-ylidene)azuleno[1,2-d][1,3]dithiole
  参考文献：
  名称：

  Azulene 基四硫富瓦烯：制备及其供电子能力

  摘要：

  The condensation reaction of dithiocarbonates derived from azuleno-and guaiazulenopentathiepin with vinylene trithiocarbonate and the ethylenedithio derivative in triethyl phosphite afforded azulene-based tetrathiafulvalenes [Az-TTF, Az-(EDT)TTF, GAz-TTF and GAz-(EDT)TTF], respectively. The vinylene derivatives (Az-TTF and GAz-TTF) showed slightly higher electron-donating ability than the corresponding ethylenedithio ones [Az-(EDT)TTF and GAz-(EDT)TTF] by CV measurement. GAz-TTFs produced charge transfer complexes with tetracyanoquinodimethane, respectively.

  DOI：

  10.3987/com-16-s(s)85
• 作为产物：
  描述：

  奥苷菊环 在 吡啶 、 lithium aluminium tetrahydride 、 cyclo-tetradecasulfur 作用下， 以 四氢呋喃 为溶剂， 反应 79.67h， 生成 Azuleno[1,2-d][1,3]dithiol-2-one
  参考文献：
  名称：

  AZULENOPENTATHIEPIN: PREPARATION AND CONVERSION INTO AZULENES WITH SULFUR GROUPS AT THE 1- AND 2-POSITIONS

  摘要：

  Azulenopentathiepin was prepared by the reaction of azulene with elemental sulfur in boiling pyridine. Bis(thiolate) generated from the pentathiepin reacted with electrophiles such as iodomethane, methyl chloroformate, N,N'-carbonyldiimidazole and N,N'-thiocarbonyldiimidazole to afford the corresponding azulene derivatives. Desulfuration of the pentathiepin and the successive reaction with DMAD or a Pd(0) reagent afforded a 1,4-dithiin compound or Pd complexes.

  DOI：

  10.3987/com-12-s(n)80

文献信息

• Azulene-Based Tetrathiafulvalenes: Preparation and Their Electron-Donating Ability
  作者：Ohki Sato、Takahito Saito、Masami Aoki、Atsushi Sakai

  DOI：10.3987/com-16-s(s)85

  日期：——

  The condensation reaction of dithiocarbonates derived from azuleno-and guaiazulenopentathiepin with vinylene trithiocarbonate and the ethylenedithio derivative in triethyl phosphite afforded azulene-based tetrathiafulvalenes [Az-TTF, Az-(EDT)TTF, GAz-TTF and GAz-(EDT)TTF], respectively. The vinylene derivatives (Az-TTF and GAz-TTF) showed slightly higher electron-donating ability than the corresponding ethylenedithio ones [Az-(EDT)TTF and GAz-(EDT)TTF] by CV measurement. GAz-TTFs produced charge transfer complexes with tetracyanoquinodimethane, respectively.
• AZULENOPENTATHIEPIN: PREPARATION AND CONVERSION INTO AZULENES WITH SULFUR GROUPS AT THE 1- AND 2-POSITIONS
  作者：Ohki Sato、Atsushi Sakai、Masami Aoki、Takaaki Kuramochi、Juzo Nakayama

  DOI：10.3987/com-12-s(n)80

  日期：——

  Azulenopentathiepin was prepared by the reaction of azulene with elemental sulfur in boiling pyridine. Bis(thiolate) generated from the pentathiepin reacted with electrophiles such as iodomethane, methyl chloroformate, N,N'-carbonyldiimidazole and N,N'-thiocarbonyldiimidazole to afford the corresponding azulene derivatives. Desulfuration of the pentathiepin and the successive reaction with DMAD or a Pd(0) reagent afforded a 1,4-dithiin compound or Pd complexes.