2-(13-Thiophen-2-yl-5,14-dihydropentacen-6-yl)thiophene | 1333867-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 2-(13-Thiophen-2-yl-5,14-dihydropentacen-6-yl)thiophene
• 英文别名: 2-(13-thiophen-2-yl-5,14-dihydropentacen-6-yl)thiophene
• CAS: 1333867-50-7
• 化学式: C₃₀H₂₀S₂
• 分子量: 444.621
• InChiKey: YMBVPWSZZMPFLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-(13-Thiophen-2-yl-5,14-dihydropentacen-6-yl)thiophene 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 甲苯 为溶剂， 反应 4.0h， 生成
  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 四(三苯基膦)钯 、 一氯化碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2-(13-Thiophen-2-yl-5,14-dihydropentacen-6-yl)thiophene
  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

文献信息

• 6,13-DIHALOGEN-5,14-DIHYDROPENTACENE DERIVATIVE AND METHOD FOR PRODUCING 6,13-SUBSTITUTED-5,14-DIHYDROPENTACENE DERIVATIVE USING SAME
  申请人：Takahashi Tamotsu

  公开号：US20130079530A1

  公开（公告）日：2013-03-28

  The present invention provides a 6,13-dihalogen-5,14-dihydropentacene derivative and a method for production thereof. Compounds (b) and (c) are reacted through cross-coupling reaction in the presence of a metal compound and a lithiating agent to synthesize compound (d), which is then halogenated to thereby obtain a 6,13-dihalogen-5,14-dihydropentacene derivative (compound (e)). [wherein X 1 and X 2 are each a halogen atom, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each a hydrogen atom, an optionally substituted C 1 -C 20 hydrocarbon group, etc.]

  本发明提供了一种6，13-二卤代-5，14-二氢戊五烯衍生物及其生产方法。通过在金属化合物和锂化剂的存在下，将化合物（b）和（c）通过交叉偶联反应反应，合成化合物（d），然后通过卤代反应获得6，13-二卤代-5，14-二氢戊五烯衍生物（化合物（e））。[其中X1和X2均为卤素原子，R1、R2、R3、R4、R5、R6、R7、R8、R9和R10均为氢原子、可选的取代的C1-C20碳氢基团等]
• Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene
  作者：Tamotsu Takahashi、Zhiying Jia、Shi Li、Kiyohiko Nakajima、Ken-ichiro Kanno、Zhiyi Song

  DOI：10.3987/com-12-s(n)130

  日期：——

  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.