4,4'-(2,2'-bithiophen-5,5'-diyl)dibenzaldehyde | 932745-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,4'-(2,2'-bithiophen-5,5'-diyl)dibenzaldehyde
• 英文别名: 4-[5-[5-(4-Formylphenyl)thiophen-2-yl]thiophen-2-yl]benzaldehyde
• CAS: 932745-70-5
• 化学式: C₂₂H₁₄O₂S₂
• 分子量: 374.484
• InChiKey: AYPWTMHKZNQHSO-UHFFFAOYSA-N

物化性质

• 熔点：
  244-246 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  558.5±50.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-(2,2'-bithiophen-5,5'-diyl)dibenzaldehyde 、 肼甲酰亚胺酰胺一氯化氢 在 三乙胺 作用下， 以 乙醇 为溶剂， 以65%的产率得到N-[4,4'-(2,2'-bithiophen-5,5'-diyl)dibenzylidene]-N'-amidinohydrazine
  参考文献：
  名称：

  Synthesis of Novel Bithiophene-Substituted Heterocycles Bearing Carbonitrile Groups

  摘要：

  Symmetrical and unsymmetrical bithiophene-substituted heterocycles bearing carbonitriles including imidazo[1,2-a]pyridine, benzimidazole, and pyridine derivatives have been synthesized via different synthetic protocols. The bithiophene bis-imidazo[1,2-a] pyridine derivatives 3a,b were achieved in three steps starting from 2-acetyl-5-bromothiophene. Suzuki coupling reaction of 2a with 5-formylthiophen-2-ylboronic acid forms the formyl derivative 5, which by condensation with 3,4-diaminobenzonitrile in the presence of sodium bisulfite furnishes the unsymmetrical bithiophene derivative6. The bis-benzimidazole derivative 8 was obtained via hexabutylditin-mediated homocoupling of 5-bromothiophene-2-carboxaldehyde, while the benzimidazole derivatives 12a,b were prepared via the formyl derivatives 11a,b, a product of Velsmier formylation reaction of 10a,b. Two synthetic protocols for the aryl/hetaryl-2,2'-bithiophene derivative 14 have also been presented. In addition, the guanyl hydrazones of bithiophenes, 16 and 17, were prepared from bis(tri-n-butylstannyl)-2,2'-bithiophene through a Stille coupling reaction followed by a condensation step.

  DOI：

  10.1080/00397910903537364
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联噻吩 、 4-甲酰基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以5.8%的产率得到4,4'-(2,2'-bithiophen-5,5'-diyl)dibenzaldehyde
  参考文献：
  名称：

  对称类芴并咪唑衍生物及其制备方法

  摘要：

  本发明涉及一种对称类芴并咪唑衍生物及其制备方法。该化合物的结构通式为：该方法便捷、普适、经济。此化合物在有机光电材料和基于荧光探测的分析领域中有广泛的应用前景；除此之外，由于该类化合物具有对称结构，使得其分子热稳定性大大提高，这样更有利于OLED发光器件的制备。

  公开号：

  CN106883182A

文献信息

• 对称类芴并咪唑衍生物及其制备方法
  申请人：上海大学

  公开号：CN106883182A

  公开（公告）日：2017-06-23

  本发明涉及一种对称类芴并咪唑衍生物及其制备方法。该化合物的结构通式为：该方法便捷、普适、经济。此化合物在有机光电材料和基于荧光探测的分析领域中有广泛的应用前景；除此之外，由于该类化合物具有对称结构，使得其分子热稳定性大大提高，这样更有利于OLED发光器件的制备。
• Synthesis of Novel Bithiophene-Substituted Heterocycles Bearing Carbonitrile Groups
  作者：Mohamed A. Ismail、David W. Boykin

  DOI：10.1080/00397910903537364

  日期：2011.1.25

  Symmetrical and unsymmetrical bithiophene-substituted heterocycles bearing carbonitriles including imidazo[1,2-a]pyridine, benzimidazole, and pyridine derivatives have been synthesized via different synthetic protocols. The bithiophene bis-imidazo[1,2-a] pyridine derivatives 3a,b were achieved in three steps starting from 2-acetyl-5-bromothiophene. Suzuki coupling reaction of 2a with 5-formylthiophen-2-ylboronic acid forms the formyl derivative 5, which by condensation with 3,4-diaminobenzonitrile in the presence of sodium bisulfite furnishes the unsymmetrical bithiophene derivative6. The bis-benzimidazole derivative 8 was obtained via hexabutylditin-mediated homocoupling of 5-bromothiophene-2-carboxaldehyde, while the benzimidazole derivatives 12a,b were prepared via the formyl derivatives 11a,b, a product of Velsmier formylation reaction of 10a,b. Two synthetic protocols for the aryl/hetaryl-2,2'-bithiophene derivative 14 have also been presented. In addition, the guanyl hydrazones of bithiophenes, 16 and 17, were prepared from bis(tri-n-butylstannyl)-2,2'-bithiophene through a Stille coupling reaction followed by a condensation step.