5-(4-acetylphenyl)-2-acetylthiophene | 92254-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-acetylphenyl)-2-acetylthiophene
• 英文别名: 1-(5-(4-acetylphenyl)thiophen-2-yl)ethan-1-one；1-[4-(5-Acetylthiophen-2-yl)phenyl]ethanone；1-[4-(5-acetylthiophen-2-yl)phenyl]ethanone
• CAS: 92254-20-1
• 化学式: C₁₄H₁₂O₂S
• 分子量: 244.314
• InChiKey: FOXXDTFJNVIVDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-acetylphenyl)-2-acetylthiophene 、 肼甲酰亚胺酰胺一氯化氢 生成
  参考文献：
  名称：

  Bis-guanylhydrazones as efficient anti-Candida compounds through DNA interaction

  摘要：

  Candida spp. are leading causes of opportunistic mycoses, including life-threatening hospital-borne infections, and novel antifungals, preferably aiming targets that have not been used before, are constantly needed. Hydrazone-and guanidinecontaining molecules have shown a wide range of biological activities, including recently described excellent antifungal properties. In this study, four bis-guanylhydrazone derivatives (BG1-4) were generated following a previously developed synthetic route. Anti-Candida (two C. albicans, C. glabrata, and C. parapsilosis) minimal inhibitory concentrations (MICs) of bisguanylhydrazones were between 2 and 15.6 mu g/mL. They were also effective against preformed 48-h-old C. albicans biofilms. In vitroDNA interaction, circular dichroism, and molecular docking analysis showed the great ability of these compounds to bind fungal DNA. Competition with DNA-binding stain, exposure of phosphatidylserine at the outer layer of the cytoplasmic membrane, and activation of metacaspases were shown for BG3. This pro-apoptotic effect of BG3 was only partially due to the accumulation of reactive oxygen species in C. albicans, as only twofold MIC and higher concentrations of BG3 caused depolarization of mitochondrial membrane which was accompanied by the decrease of the activity of fungal mitochondrial dehydrogenases, while the activity of oxidative stress response enzymes glutathione reductase and catalase was not significantly affected. BG3 showed synergistic activity with amphotericin B with a fractional inhibitory concentration index of 0.5. It also exerted low cytotoxicity and the ability to inhibit epithelial cell (TR146) invasion and damage by virulent C. albicans SC5314. With further developments, BG3 may further progress in the antifungal pipeline as a DNA-targeting agent.

  DOI：

  10.1007/s00253-018-8749-3
• 作为产物：
  描述：

  2-乙酰基-5-溴噻吩 、 4-碘代苯乙酮 在 potassium phosphate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以70%的产率得到5-(4-acetylphenyl)-2-acetylthiophene
  参考文献：
  名称：

  Visible light induced cross-coupling synthesis of asymmetrical heterobiaryls using Pd/CeO2 nanocomposite photocatalyst

  摘要：

  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.

  DOI：

  10.1016/j.cclet.2018.01.002

文献信息

• The first use of [PdBr2(imidazolidin-2-ylidene)(pyridine)] catalysts in the direct C-H bond arylation of C2-substituted furan and thiophene
  作者：Murat Kaloğlu、Nazan Kaloğlu、Namık Özdemir、İsmail Özdemir

  DOI：10.1007/s11164-021-04444-4

  日期：2021.7

  was determined by single-crystal X-ray diffraction study. The catalytic activities of all palladium complexes were evaluated in the direct C-H bond arylation of the 2-acetylfuran and 2-acetylthiophene with (hetero) aryl bromides and readily available and inexpensive aryl chlorides in presence of 1 mol% catalyst loading at 120 °C. Under the given conditions, (hetero)aryl halides were successfully applied

  摘要 ñ-杂环卡宾（NHC）连接的PEPPSI型钯络合物最近已用于杂芳烃的直接CH键芳基化。然而，在大多数已发表的著作中，已经使用了含有苯并咪唑和咪唑环的NHC配体，但是很少使用含有饱和咪唑啉环的NHC配体。因此，在这项研究中，合成了四种新的1,3-二取代的咪唑啉盐作为NHC配体前体，以及它们的四种新的PEPPSI型钯配合物。所有新化合物的结构均通过不同的光谱和分析技术进行了全面表征。钯配合物之一的更详细的结构表征是通过单晶X射线衍射研究确定的。在120℃下，负载1 mol％催化剂的条件下，在2-乙酰基呋喃和2-乙酰基噻吩与（杂）芳基溴化物和易得且廉价的芳基氯化物的直接CH键芳基化反应中，评估了所有钯配合物的催化活性。在给定的条件下，成功地使用了（杂）芳基卤化物作为芳基化试剂，以可接受的高收率获得了C5芳基化的呋喃和噻吩。 图形摘要
• Ligand-less palladium-catalyzed direct 5-arylation of thiophenes at low catalyst loadings
  作者：Julien Roger、Franc Požgan、Henri Doucet

  DOI：10.1039/b819912d

  日期：——

  Ligand-less Pd(OAc)2 provides a very efficient catalyst for the direct 5-arylation of thiophene derivatives. With this catalyst, a low palladium concentration (0.1–0.001 mol%) should be employed in order to obtain high yields of coupling products. At higher concentrations a fast formation of inactive “Pd black” generally occurs. Substrates/catalysts ratios up to 100000 can be employed with the most

  配体较少的Pd（OAc）2提供了非常有效的催化剂 用于直接的5-芳基化 噻吩衍生品。有了这个催化剂低 钯为了获得高收率的偶联产物，应使用浓度（0.1–0.001 mol％）的溶液。在较高浓度下，通常会快速形成无活性的“钯黑”。基材/催化剂活性最高的芳基溴化物可使用高达100000的比例。两个偶合伙伴都可以容忍各种各样的官能团。该反应的主要浪费是与KOAc有关的HBr。因此，该方法比采用有机金属衍生物的传统交叉偶联方法在经济和环境上更具吸引力。
• Arylation of heterocyclic compounds by benzimidazole-based N-heterocyclic carbene-palladium(II) complexes
  作者：Neslihan Şahin、Nevin Gürbüz、Hande Karabıyık、Hasan Karabıyık、İsmail Özdemir

  DOI：10.1016/j.jorganchem.2019.121076

  日期：2020.2

  compounds were fully characterized by 1H, 13C1H} NMR and FT-IR spectra. The structures of 2c, 2d, and 2e were determined by X-ray crystallography and the prepared complexes (2a-e) were investigated as catalysts for the direct arylation of 2-n-propylthiazole, 4,5-dimethylthiazole and 2-acetylthiophene with various aryl bromides. High catalytic activity for arylation was seen reaction using only 0.5 mol%

  在富含电子的杂芳烃的情况下，可以使用芳基卤化物活化特定的C H键进行芳基化，而无需指导该基团。容易产生卤素取代的芳基化杂芳烃的能力在有机化学中很重要，因为这些物种是生物化学家的重要组成部分。在此手稿中，我们报告了P​​EPPSI型新型苯并咪唑基N-杂环卡宾-钯（II）配合物（2a-e）的合成。所有这些新化合物均通过1 H，13 C 1 H} NMR和FT-IR光谱进行了全面表征。通过X射线晶体学确定2c，2d和2e的结构，并制备配合物（研究了2a-e）作为2-正丙基噻唑，4，5-二甲基噻唑和2-乙酰基噻吩与各种芳基溴直接芳基化的催化剂。仅使用0.5mol％的催化剂反应1小时，观察到高的芳基化催化活性。
• Synthesis, structures and catalytic activity of Pd(II) saccharinate complexes with monophosphines in direct arylation of five-membered heteroarenes with aryl bromides
  作者：Veysel T. Yilmaz、Ceyda Icsel、Omer R. Turgut、Muhittin Aygun、Enes Evren、Ismail Ozdemir

  DOI：10.1016/j.ica.2019.119220

  日期：2020.1

  substituted tertiary phosphine ligands with systematically changing electronic and steric properties, namely trans-[PdCl(sac)(L)2] (L = PPh3 (1); PPh2Cy (3)), trans-[Pd(sac)2(H2O)(L)] (L = PPh3 (2); PPh2Cy (5)), trans-[Pd(sac)2(L)2] (L = PPh2Cy (4); PPhCy2 (6); PCy3 (8)), [PdCl(sac)(PCy3)(DMSO)] (7), trans-[Pd(sac)2(PPh2Me)(DMSO)] (9) and cis-[M(sac)2(L)2] (L = PPhMe2 (10); PPh2Et (11); PPhEt2 (12)), were

  摘要许多具有一系列被苯基（Ph），环己基（Cy）和烷基（Me和Et）取代的叔膦配体的新型Pd（II）糖精（sac）配合物，其电子和空间特性发生了系统性的变化，即反式[[ PdCl（sac）（L）2]（L = PPh3（1）; PPh2Cy（3）），反式[Pd（sac）2（H2O）（L）]（L = PPh3（2）; PPh2Cy（5） ），反式[Pd（sac）2（L）2]（L = PPh2Cy（4）; PPhCy2（6）; PCy3（8）），[PdCl（sac）（PCy3）（DMSO）]（7），反式[Pd（sac）2（PPh2Me）（DMSO）]（9）和顺式[M（sac）2（L）2]（L = PPhMe2（10）; PPh2Et（11）; PPhEt2（12）） ，合成和结构表征。将Pd（II）配合物用于五元杂芳烃（例如呋喃，噻吩和噻唑衍生物）与芳基溴化物的直接C2 / C5芳基化。值得注意
• Well‐defined PEPPSI‐themed palladium–NHC complexes: synthesis, and catalytic application in the direct arylation of heteroarenes
  作者：Murat Kaloğlu、Nevin Gürbüz、İlkay Yıldırım、Namık Özdemir、İsmail Özdemir

  DOI：10.1002/aoc.5387

  日期：2020.2

  synthesis of the PEPPSI (pyridine enhanced precatalyst preparation stabilization and initiation)‐themed, six new Pd‐complexes with the general formula [PdX2(NHC)(pyridine)]. The structures of all compounds were characterized by various spectroscopic techniques such as 1H NMR, 13C NMR and FT‐IR. The more detailed structural characterization of four of the complexes was determined by single‐crystal X‐ray

  在这项研究中，合成了一系列苯并咪唑鎓盐作为不对称的N杂环卡宾（NHC）前体。苯并咪唑盐用于合成以PEPPSI（吡啶增强的前催化剂制剂的稳定和引发作用）为主题的六种新型Pd配合物，其通式为[PdX 2（NHC）（吡啶）]。所有化合物的结构均通过各种光谱技术进行了表征，例如1 H NMR，13C NMR和FT‐IR 通过单晶X射线衍射研究确定了四种配合物的更详细的结构表征。在负载量为1 mol％的情况下，在2-乙酰基呋喃和2-乙酰基噻吩与芳基溴的直接芳基化反应中，评估了所有Pd络合物的催化活性。