4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene | 1523510-28-2

• 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-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene
• 英文别名: 7-Octylidene-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene；7-octylidene-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 1523510-28-2
• 化学式: C₁₇H₂₀S₂
• 分子量: 288.478
• InChiKey: YHSIXCKHDRXQLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴代异辛烷 、 4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到4-(2-ethylhexyl)-4-octyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene
  参考文献：
  名称：

  Synthetic Routes toward Asymmetrically Substituted (Functionalized) 4H-Cyclopenta[2,1-b:3,4-b′]dithiophenes

  摘要：

  A two-step synthetic protocol involving (i) a Wittig-type carbonyl olefination, and (ii) regioselective alkylation of the exocyclic double bond with LiAlH4 and an alkyl bromide, was developed as an alternative to the recently reported three-step synthetic approach toward asymmetrically substituted/functionalized 4H-cyclopenta[2,1-b:3,4-b]dithiophenes. The two routes are rather complementary, with specific advantages depending on the desired substitution pattern, and are of particular appeal for the construction of semiconducting materials to be applied in organic photovoltaics.

  DOI：

  10.1055/s-0033-1339707
• 作为产物：
  描述：

  4H-环戊并[2,1-B:3,4-B']二噻吩-4-酮 、 (1-辛基)三苯基溴化磷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以74%的产率得到4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene
  参考文献：
  名称：

  Synthetic Routes toward Asymmetrically Substituted (Functionalized) 4H-Cyclopenta[2,1-b:3,4-b′]dithiophenes

  摘要：

  A two-step synthetic protocol involving (i) a Wittig-type carbonyl olefination, and (ii) regioselective alkylation of the exocyclic double bond with LiAlH4 and an alkyl bromide, was developed as an alternative to the recently reported three-step synthetic approach toward asymmetrically substituted/functionalized 4H-cyclopenta[2,1-b:3,4-b]dithiophenes. The two routes are rather complementary, with specific advantages depending on the desired substitution pattern, and are of particular appeal for the construction of semiconducting materials to be applied in organic photovoltaics.

  DOI：

  10.1055/s-0033-1339707