1,4-双(3-噻吩基)苯 | 37913-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,4-双(3-噻吩基)苯
• 英文名称: 1,4-di(thiophen-3-yl)benzene
• 英文别名: p-di(thiophen-3-yl)benzene；1,4-bis(3-thienyl)benzene；1,4-di(3-thienyl)benzene；1,4-Di(thiophen-3-yl)benzene；3-(4-thiophen-3-ylphenyl)thiophene
• CAS: 37913-76-1
• 化学式: C₁₄H₁₀S₂
• 分子量: 242.365
• InChiKey: WTCJNWRAJYMGKI-UHFFFAOYSA-N

物化性质

• 熔点：
  281-282 °C
• 沸点：
  350.0±22.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,4-双(3-噻吩基)苯 在 镍 氢气 作用下， 生成 1,4-二(丁烷-2-基)苯
  参考文献：
  名称：

  Ribereau,P. et al., Bulletin de la Societe Chimique de France, 1972, p. 1581 - 1587

  摘要：

  DOI：
• 作为产物：
  描述：

  3-噻吩硼酸 、 1,4-二溴苯 在 C₁₄H₈F₆O₄ 、 nickel trifluoroacetate 、 potassium carbonate 、 三苯基膦 、 1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺 作用下， 以 水 为溶剂， 反应 18.0h， 以62.1%的产率得到1,4-双(3-噻吩基)苯
  参考文献：
  名称：

  在离子液体中镍催化的芳基卤化物与芳基硼酸的铃木-宫浦交叉偶联反应

  摘要：

  在环境友好的反应介质中，已经开发了镍催化的联芳基和三联苯合成的有效策略。在存在β-二酮和PPh 3配体的情况下，Ni（TFA）2充当离子液体溶液中芳基卤化物和芳基硼​​酸的Suzuki-Miyaura交叉偶联的有效催化剂。在该催化体系下，以高收率获得了联芳基和三联苯。

  DOI：

  10.1016/j.catcom.2014.08.037

文献信息

• Preparation of 1,4-Bis[2-{2-(1-methyl-1H-imidazol-5-yl)ethynyl}-3-thienyl]benzene and Related Compounds
  作者：Kozo Toyota、Kazuyuki Okada、Yasutomo Tsuji、Noboru Morita、Hiroshi Katsuta

  DOI：10.3987/com-08-s(f)84

  日期：——

  1,4-Bis[2-2-(l-methyl-1H-imidazol-5-yl)ethynyl}-3-thienyl]benzene, l,4-bis[2-(2-ferrocenylethynyl)-3-thienyl]benzene, and some related compounds were prepared and their UV-visible spectra were studied.

  1,4-双[2-2-(1-甲基-1H-咪唑-5-基)乙炔基}-3-噻吩基]苯,1,4-双[2-(2-二茂铁乙炔基)-3-噻吩基]苯，并制备了一些相关化合物，并研究了它们的紫外-可见光谱。
• Chemistry of Bis(2-ethynyl-3-thienyl)arene and Related Systems, Part 5: Preparation of an Unsymmetrical 4,4’-Bis(3-thienyl)biphenyl Derivative Containing a 2-[2-(Diphenylphosphino)ethynyl]-3-thienyl Moiety
  作者：Kozo Toyota、Yasutomo Tsuji、Noboru Morita

  DOI：10.1080/10426501003772037

  日期：2010.5.27

  An unsymmetrically substituted 4,4′-bis(3-thienyl)biphenyl derivative of 4-(2-ethynyl-3-thienyl)-4′-(3-thienyl)biphenyl type was prepared, utilizing 4-bromo-4′-(2-iodo-3-thienyl) biphenyl as synthetic intermediate. Reaction of 4-(2-ethynyl-3-thienyl)-4′-(3-thienyl) biphenyl with ethylmagnesium bromide followed by treatment with chlorodiphenylphosphine afforded 4-[2-(2-diphenylphosphinoethynyl)-3-t

  利用4-溴-4'-制备了4-(2-乙炔基-3-噻吩基)-4'-(3-噻吩基)联苯型的不对称取代的4,4'-双(3-噻吩基)联苯衍生物。 (2-iodo-3-thienyl) 联苯作为合成中间体。4-(2-乙炔基-3-噻吩基)-4'-(3-噻吩基)联苯与溴化乙基镁反应，然后用氯二苯基膦处理，得到4-[2-(2-二苯基膦基乙炔基)-3-噻吩基]-4' -(3-噻吩基)联苯。
• Rhodium-Catalyzed Dehydrogenative Coupling of Phenylheteroarenes with Alkynes or Alkenes
  作者：Tomonori Iitsuka、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/acs.joc.5b00155

  日期：2015.3.6

  Benzo-fused tri- to heptacyclic heteroarenes were effectively constructed by the rhodium-catalyzed dehydrogenative coupling of phenylheteroarenes with alkynes. Using alkenes as coupling partners, dehydrogenative alkenylation took place selectively on the phenyl moiety of phenylheteroarenes. Several experiments with deuterium-labeled substrates indicated that double C-H bond cleavages take place even in the reaction with alkenes.
• Preparation of 1,4-bis(2-ethynyl-3-thienyl)benzenes as versatile spacers for connection of heterocycles
  作者：K TOYOTA、Y GOTO、K OKADA、N MORITA

  DOI：10.1016/s0385-5414(07)81098-7

  日期：2007.10.1

  Iodination of 1,4-di(3-thienyl)benzene gave 1,4-bis(2-iodo-3-thienyl)benzene, which was converted to 1,4-bis(2-ethynyl-3-thienyl)benzene. Novel 1,4-bis[2-(pyridylethynyl)-3-thienyl]benzene ligands containing the bis(ethynylthienyl)benzene spacer were prepared by Sonogashira reaction. Advantage of the spacer was demonstrated by introducing functionalized alkyl groups to the 5-position of the thiciphene ring of 1,4-bisl2-(trialkylsilylethynyl)-3-thienyl]benzene.
• Nickel-catalysed Suzuki–Miyaura cross-coupling reactions of aryl halides with arylboronic acids in ionic liquids
  作者：Man Wang、Xiaobin Yuan、Hongyu Li、Limin Ren、Zhizhong Sun、Yanjun Hou、Wenyi Chu

  DOI：10.1016/j.catcom.2014.08.037

  日期：2015.1

  An efficient strategy for the nickel-catalysed synthesis of biaryls and terphenyls has been developed in environmentally-friendly reaction media. In the presence of β-diketone and PPh3 ligands, Ni(TFA)2 acted as an effective catalyst for the Suzuki–Miyaura cross-coupling of aryl halides and arylboronic acids in an ionic liquid solution. Biaryls and terphenyls were obtained in good yields under this

  在环境友好的反应介质中，已经开发了镍催化的联芳基和三联苯合成的有效策略。在存在β-二酮和PPh 3配体的情况下，Ni（TFA）2充当离子液体溶液中芳基卤化物和芳基硼​​酸的Suzuki-Miyaura交叉偶联的有效催化剂。在该催化体系下，以高收率获得了联芳基和三联苯。