(E,E)-1-(2-benzo[b]thienyl)-4-(p-tolyl)-1,2,3,4-tetrafluoro-1,3-butadiene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (E,E)-1-(2-benzo[b]thienyl)-4-(p-tolyl)-1,2,3,4-tetrafluoro-1,3-butadiene
• 英文别名: 2-[(1E,3E)-1,2,3,4-tetrafluoro-4-(4-methylphenyl)buta-1,3-dienyl]-1-benzothiophene
• 化学式: C₁₉H₁₂F₄S
• 分子量: 348.364
• InChiKey: DOMYLJLKUCXDSJ-YWNVXTCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzothiophen-2-yllithium 、 1-(p-tolyl)-1,2,3,4,4-pentafluoro-1,3-butadiene 生成 (E,E)-1-(2-benzo[b]thienyl)-4-(p-tolyl)-1,2,3,4-tetrafluoro-1,3-butadiene
  参考文献：
  名称：

  Synthesis of Conjugated F-Polyenes Containing Thienyl Ring Systems

  摘要：

  Novel 1-substituted F-1,3-butadienes ThioAr-CF=CFCF=CF2, ThioAr = 2-thienyl and 2-benzo[b]thienyl, and symmetrically 1,4-disubstituted F-1,3-butadienes ThioAr-CF=CFCF=CF-ThioAr, ThioAr = 5-R'-2-thienyl (R' = Me, SiMe3, CF=CFCl), 3-thienyl, and 4-dibenzo[b,d]thienyl, inclusive of the above-named substituents, were prepared by the reaction of organolithium derivatives with F-1,3-butadiene (PFBD). Monothioaryl-substituted F-1,3-butadienes were used as intermediates in subsequent reactions with other (thioaryl)organolithium derivatives for the synthesis of a new series of unsymmetrically substituted alpha,omega-bis(thioaryl)-F-polyenes ThioAr-(CF=CF)(n)-ThioAr', where n = 2, ThioAr, ThioAr' = 4-RC2H4 (R = H, Me, OC6H11, NMe2), 2-thienyl, 5-methyl-2-thienyl, 2-benzo[b]thienyl, 4-dibenzo[b,d]thienyl, and for n = 3, ThioAr = 2-thienyl, ThioAr' = 5-methyl-2-thienyl. The reaction of 2,5-dilithiothiophene with 1-(2-thienyl)-F-1,3-butadiene affords 2,5-bis-[4-(2-thienyl)-1,2,3,4-tetrafluoro-1,3-butadienyl]thiophene (5). 2,5-Thienylene-F-polyenylene polymers were prepared by the reaction of 2,5-dilithio- and 2,5-bis(bromomagnesio)thiophene derivatives with PFBD and F-ethylene. The oligomers 5 and 2,5-bis[2-(2-thienyl)-1,2-difluoroethylenyl]- thiophene (16) were found to possess liquid crystalline properties. The reaction of 1,4-bis(2-thienyl)-F-1,3-butadiene with nitric acid led to substitution in one or in both thienyl rings at position 5. NMR, electronic spectra, and structural aspects of the title compounds are discussed.

  DOI：

  10.1021/jo962325x

文献信息

• Synthesis of Conjugated <i>F</i>-Polyenes Containing Thienyl Ring Systems
  作者：Alexander B. Shtarev、Zdeněk Chvátal

  DOI：10.1021/jo962325x

  日期：1997.8.1

  Novel 1-substituted F-1,3-butadienes ThioAr-CF=CFCF=CF2, ThioAr = 2-thienyl and 2-benzo[b]thienyl, and symmetrically 1,4-disubstituted F-1,3-butadienes ThioAr-CF=CFCF=CF-ThioAr, ThioAr = 5-R'-2-thienyl (R' = Me, SiMe3, CF=CFCl), 3-thienyl, and 4-dibenzo[b,d]thienyl, inclusive of the above-named substituents, were prepared by the reaction of organolithium derivatives with F-1,3-butadiene (PFBD). Monothioaryl-substituted F-1,3-butadienes were used as intermediates in subsequent reactions with other (thioaryl)organolithium derivatives for the synthesis of a new series of unsymmetrically substituted alpha,omega-bis(thioaryl)-F-polyenes ThioAr-(CF=CF)(n)-ThioAr', where n = 2, ThioAr, ThioAr' = 4-RC2H4 (R = H, Me, OC6H11, NMe2), 2-thienyl, 5-methyl-2-thienyl, 2-benzo[b]thienyl, 4-dibenzo[b,d]thienyl, and for n = 3, ThioAr = 2-thienyl, ThioAr' = 5-methyl-2-thienyl. The reaction of 2,5-dilithiothiophene with 1-(2-thienyl)-F-1,3-butadiene affords 2,5-bis-[4-(2-thienyl)-1,2,3,4-tetrafluoro-1,3-butadienyl]thiophene (5). 2,5-Thienylene-F-polyenylene polymers were prepared by the reaction of 2,5-dilithio- and 2,5-bis(bromomagnesio)thiophene derivatives with PFBD and F-ethylene. The oligomers 5 and 2,5-bis[2-(2-thienyl)-1,2-difluoroethylenyl]- thiophene (16) were found to possess liquid crystalline properties. The reaction of 1,4-bis(2-thienyl)-F-1,3-butadiene with nitric acid led to substitution in one or in both thienyl rings at position 5. NMR, electronic spectra, and structural aspects of the title compounds are discussed.