2-benzoylbithiophene | 58400-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoylbithiophene
• 英文别名: (2,2'-bithiophen-5-yl)(phenyl)methanone；2,2'-bithien-5-yl(phenyl)methanone；phenyl[2,2'-bithiophen-5-yl]methanone；Phenyl-(5-thiophen-2-ylthiophen-2-yl)methanone
• CAS: 58400-12-7
• 化学式: C₁₅H₁₀OS₂
• 分子量: 270.376
• InChiKey: HNRPVXHYXBHAKA-UHFFFAOYSA-N

物化性质

• 熔点：
  74-76 °C(Solv: pentane (109-66-0))
• 沸点：
  435.5±35.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoylbithiophene 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 以93%的产率得到(E)-1,2-di(2,2'-bithiophen-5-yl)-1,2-diphenylethene
  参考文献：
  名称：

  Oligothiophenes III: Synthesis of Tetra‐thienyl‐Substituted Ethylenes Including an Abnormal McMurry Coupling Result

  摘要：

  This article describes the synthesis of some selected tetra-thiophenyl-substituted ethenes by McMurry coupling of some selected thienyl ketones, including a surprising coupling product. The products were analyzed by MS, NMR, UV, and x-ray crystallography. Their cyclic voltagrams were recorded.

  DOI：

  10.1080/00397910701199037
• 作为产物：
  描述：

  2,2'-联二噻吩 、 苯甲腈 在 正丁基锂 、 盐酸 作用下， 以 乙醚 、 正己烷 、 苯 为溶剂， 反应 17.0h， 以63%的产率得到2-benzoylbithiophene
  参考文献：
  名称：

  Oligothiophenes III: Synthesis of Tetra‐thienyl‐Substituted Ethylenes Including an Abnormal McMurry Coupling Result

  摘要：

  This article describes the synthesis of some selected tetra-thiophenyl-substituted ethenes by McMurry coupling of some selected thienyl ketones, including a surprising coupling product. The products were analyzed by MS, NMR, UV, and x-ray crystallography. Their cyclic voltagrams were recorded.

  DOI：

  10.1080/00397910701199037

文献信息

• Synthesis of Functionalized 2-Arylthiophenes with Triarylbismuths as Atom-Efficient Multicoupling Organometallic Nucleophiles under Palladium Catalysis
  作者：Maddali Rao、Debasis Banerjee、Ritesh Dhanorkar

  DOI：10.1055/s-0030-1260554

  日期：2011.6

  Atom-efficient cross-coupling reactions of functionalized 2-bromo- and 2-iodothiophenes have been demonstrated using triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium-catalyzed conditions. These couplings with various functionalized triarylbismuths proceeded smoothly to afford the corresponding functionalized 2-arylthiophenes in high yields.

  在钯催化条件下，使用三芳基铋作为原子效率多偶联有机金属亲核试剂，已经证明了官能化 2-溴和 2-碘噻吩的原子效率交叉偶联反应。这些与各种官能化三芳基铋的偶联顺利进行，以高产率提供相应的官能化 2-芳基噻吩。
• Highly soluble and thermally stable alkyl-free star-shaped D-π-A oligomer with electron-withdrawing phenyldicyanovinyl groups for organic photovoltaics
  作者：Yuriy N. Luponosov、Alexander N. Solodukhin、Artur L. Mannanov、Vasiliy A. Trukhanov、Svetlana M. Peregudova、Sergey A. Pisarev、Artem V. Bakirov、Maxim A. Shcherbina、Sergei N. Chvalun、Dmitry Yu Paraschuk、Sergei A. Ponomarenko

  DOI：10.1016/j.orgel.2017.09.014

  日期：2017.12

  Synthesis of the first star-shaped donor-acceptor oligomer with phenyldicyanovinyl electron-withdrawing units, namely N(Ph-2T-DCV-Ph)3, is reported. The physical and photovoltaic properties of this molecule were comprehensively studied and compared to those of the full analogues having either dicyanovinyl (N(Ph-2T-DCV)3) or alkyldicyanovinyl (N(Ph-2T-DCV)3) groups. The novel alkyl-free molecule, N(Ph-2T-DCV-Ph)3

  报道了具有苯基二氰基乙烯基吸电子单元即N（Ph-2T-DCV-Ph）3的第一星形供体-受体低聚物的合成。该分子的物理和光伏特性进行了综合研究和比较那些具有或者二氰基乙烯基（满类似物的N（PH-2T-DCV）3）或alkyldicyanovinyl（N（PH-2T-DCV）3）基团。新型无烷基分子N（Ph-2T-DCV-Ph）3显示出记录的高热稳定性，良好的溶解性，高结晶度和有希望的光伏性能作为有机体高容量异质结有机太阳能电池中的电子给体材料的幸运组合。开路电压为1.01 V.
• Krishnaswamy, N. R.; Kumar, Ch. Siva Sai Ramana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 7, p. 766 - 771
  作者：Krishnaswamy, N. R.、Kumar, Ch. Siva Sai Ramana

  DOI：——

  日期：——
• Oligothiophenes III: Synthesis of Tetra‐thienyl‐Substituted Ethylenes Including an Abnormal McMurry Coupling Result
  作者：Harald Halvorsen、Jan Skramstad、Håkon Hope

  DOI：10.1080/00397910701199037

  日期：2007.4.1

  This article describes the synthesis of some selected tetra-thiophenyl-substituted ethenes by McMurry coupling of some selected thienyl ketones, including a surprising coupling product. The products were analyzed by MS, NMR, UV, and x-ray crystallography. Their cyclic voltagrams were recorded.