1-(5-(4-nitrophenyl)thiophen-2-yl)ethanone | 61430-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(5-(4-nitrophenyl)thiophen-2-yl)ethanone
• 英文别名: 1-[5-(4-Nitrophenyl)thiophen-2-yl]ethanone
• CAS: 61430-75-9
• 化学式: C₁₂H₉NO₃S
• 分子量: 247.274
• InChiKey: WWIPEKMAOOJOSK-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  441.0±35.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-nitrobenzenediazonium tetrafluoroborate 、 5-乙酰基-2-噻吩硼酸 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 5.0h， 以84%的产率得到1-(5-(4-nitrophenyl)thiophen-2-yl)ethanone
  参考文献：
  名称：

  负载在二氧化钛纤维素复合材料（PdNPs @ TiO 2 –Cell）上的钯纳米粒子可实现无配体碳-碳交叉偶联反应†

  摘要：

  可以通过简单干净的方法合成负载在TiO 2-纤维素复合材料（PdNPs @ TiO 2 -Cell）上的直径39-45 nm的分散良好的非球形PdNP。通过XRD，FE-SEM，EDS和TEM技术对催化剂进行了很好的表征。PdNP在TiO 2-电池载体上具有良好的分散性。这导致在较低温度下使用低Pd负载量（1 mol％）合成联苯，丙烯酸酯，乙炔和前手性酮具有出色的催化活性。碱的性质和用量，溶剂的性质，催化剂的用量和反应温度对PdNPs @ TiO 2活性的影响–对细胞进行了彻底的调查。该催化剂显示出至少四倍的可重复使用性，而没有降低催化活性。

  DOI：

  10.1039/c5ra20680d

文献信息

• Microwave-assisted, ligand-free, direct C–H arylation of thiophenes in biomass-derived γ-valerolactone
  作者：Silvia Tabasso、Emanuela Calcio Gaudino、Laura Rinaldi、Audrey Ledoux、Paolo Larini、Giancarlo Cravotto

  DOI：10.1039/c7nj01540b

  日期：——

  Pd-catalyzed C–H arylation of heterocycles with aryl halides is a straightforward and more environmentally-friendly route to the synthesis of well-defined, pi-conjugated polymers for challenging applications in electronic devices. Although this type of transformation is more atom efficient than cross-couplings, it still poses environmental issues in the form of reaction media and the use of phosphine ligands

  Pd催化的杂环与芳基卤化物的C–H芳基化是合成明确定义的pi共轭聚合物的一种直接且对环境更友好的途径，可用于具有挑战性的电子设备中。尽管这种转化比交叉偶联在原子效率上更高，但它仍然以反应介质和膦配体的使用形式带来了环境问题。这项工作报道了噻吩的CH芳基化过程，对环境的影响大大改善，并且该方案有望用于合成规则的聚噻吩。γ-戊内酯（GVL）是一种无毒的生物质衍生溶剂，已用于该无膦微波辅助工艺中，并替代了常用的偶极非质子介质。活化的芳基溴化物以良好的收率得到芳基噻吩，而当存在吸电子基团时，使用碘化物并添加新戊酸。该反应还扩展到CH（杂）芳基化缩聚反应，使用低Pd负载量，以高收率和短反应时间获得了良好的区域规整性，从而获得了高分子量的聚（3-己基）噻吩。计算研究揭示了GVL在催化体系中作为配体的作用。
• Synthesis of heterocycles on the basis of arylation products of unsaturated compounds. 19.* Arylation of 2-acetylthio- phene and the synthesis of 2-(5-aryl-2-thien- yl)-4-quinolinecarboxylic acids
  作者：V. S. Matiychuk、N. D. Obushak、R. Z. Lytvyn、Yu. I. Horak

  DOI：10.1007/s10593-010-0468-3

  日期：2010.5

  arenediazonium chlorides in the presence of cupric chloride as catalyst gives 2-acetyl-5-arylthiophenes. These products react with 5-chloro- and 5-bromoisatins to give 6-chloro- and 6-bromo-substituted 2-(5-aryl-2-thienyl)-4-quinolinecarboxylic acids.

  在氯化铜作为催化剂的存在下，2-乙酰基噻吩与乙酰基噻吩与氯化壬二唑鎓的反应产生了2-乙酰基-5-芳基噻吩。这些产物与5-氯-和5-溴靛红反应，得到6-氯和6-溴取代的2-（5-芳基-2-噻吩基）-4-喹啉羧酸。
• Visible light induced cross-coupling synthesis of asymmetrical heterobiaryls using Pd/CeO2 nanocomposite photocatalyst
  作者：Yanqin Ge、Pinhui Diao、Chen Xu、Nannan Zhang、Cheng Guo

  DOI：10.1016/j.cclet.2018.01.002

  日期：2018.6

  A simple, mild and green approach has been developed for the synthesis of asymmetrical heterobiaryls under the irradiation of visible light without any oxidants and promoting reagents through using Pd/CeO2 nanocomposite photocatalyst. This method can tolerate considerable functional groups such as electron donating groups and electron-withdrawing groups through C-C cross-coupling. Moreover, we obtain the products with moderate yields in an efficient way. Finally, a plausible mechanism is proposed. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• From agriculture residue to catalyst support; A green and sustainable cellulose-based dip catalyst for C C coupling and direct arylation
  作者：Vishal Kandathil、Manjunatha Kempasiddaiah、Sasidhar B. S.、Siddappa A. Patil

  DOI：10.1016/j.carbpol.2019.115060

  日期：2019.11

  The core characteristics of a perfect catalyst include good activity, simple design, excellent stability, easy recovery from reaction mixture, recyclability, and have the provision for easy scale up. The ease in synthesis, recyclability and scale up makes the dip catalyst a major contender in this regard which possess most of the aforementioned characteristics. In this work, we report a dip catalyst made of cellulose, isolated from agriculture residue (sugarcane bagasse), in which biogenically synthesized palladium nanoparticles were dispersed. The prepared dip catalyst was characterized by FESEM, EDS, XRD, ATR-IR, TGA, TEM, XPS and ICP-OES analysis. Also, the activity of the dip catalyst was studied in the Suzuki-Miyaura cross-coupling reaction and was found to give excellent conversion with 15 recycles. Further, the activity of dip catalyst in C5-arylation of 2-substituted thiophenes was evaluated for which promising yields were obtained.