18,19-dichloro-6,13-dimethyl-17,20-dioxo-6,13-dihydro-6,13-[1,2]benzenopentacene-15,16-dicarbonitrile | 1448354-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 18,19-dichloro-6,13-dimethyl-17,20-dioxo-6,13-dihydro-6,13-[1,2]benzenopentacene-15,16-dicarbonitrile
• CAS: 1448354-77-5
• 化学式: C₃₂H₁₈Cl₂N₂O₂
• 分子量: 533.413
• InChiKey: RCPWFJHVMRUHED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  38.0
• 可旋转键数：
  0.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.72
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  18,19-dichloro-6,13-dimethyl-17,20-dioxo-6,13-dihydro-6,13-[1,2]benzenopentacene-15,16-dicarbonitrile 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以45%的产率得到6,13-dimethylpentacene
  参考文献：
  名称：

  Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene

  摘要：

  Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.

  DOI：

  10.3987/com-12-s(n)130
• 作为产物：
  描述：

  6,13-bis(trimethylsilyl)-5,14-dihydropentacene 在 bis-triphenylphosphine-palladium(II) chloride 、 一氯化碘 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 29.0h， 生成 18,19-dichloro-6,13-dimethyl-17,20-dioxo-6,13-dihydro-6,13-[1,2]benzenopentacene-15,16-dicarbonitrile
  参考文献：
  名称：

  Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene

  摘要：

  Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.

  DOI：

  10.3987/com-12-s(n)130