(Z)-4-((5-methylthiophen-2-yl)methylene)-2-phenyloxazol-5(4H)-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-4-((5-methylthiophen-2-yl)methylene)-2-phenyloxazol-5(4H)-one
• 英文别名: (4Z)-4-((5-methylthiophen-2-yl)methylene)-2-phenyloxazol-5(4H)-one；(Z)-4-[(5-methylthien-2-yl)methylene]-2-phenyloxazol-5(4H)-one；(4Z)-4-[(5-methylthiophen-2-yl)methylidene]-2-phenyl-1,3-oxazol-5-one
• 化学式: C₁₅H₁₁NO₂S
• 分子量: 269.324
• InChiKey: BQRHRIOJVGAWQK-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-4-((5-methylthiophen-2-yl)methylene)-2-phenyloxazol-5(4H)-one 在 sodium hydroxide 、 氢溴酸 作用下， 以 甲醇 为溶剂， 生成 (E)-2-benzamido-3-(5-methylthiophen-2-yl)prop-2-enoic acid
  参考文献：
  名称：

  Synthesis and Stereospecific Ring Opening of the (Z/E)-Isomers of 2-Methyl(Phenyl)-4-(thienylmethylene)-5(4H)-oxazolones

  摘要：

  DOI：

  10.1055/s-1983-30556
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 、 马尿酸 在 乙酸酐 作用下， 反应 0.2h， 以93%的产率得到(Z)-4-((5-methylthiophen-2-yl)methylene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  [C6(MIm)2]2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition

  摘要：

  摘要 二水合二[1,6-双(3-甲基咪唑鎓-1-基)己烷]十钨酸[C6(MIm)2]2W10O32·2H2O，作为一类新型多金属氧酸盐基双阳离子离子液体(POM-DIL)，被合成并应用于在超声辅助无溶剂条件下合成4-芳亚甲基-2-苯基-5(4)-噁唑酮(吡唑啉酮)的有效非均相催化剂。基于实验结果，该反应在温和条件下获得了极佳的产率。简便的工作流程和纯化使其在经济角度上具有很高的吸引力。此外，循环利用研究证实了该催化剂可以多次重复使用而不会显著损失其活性。

  DOI：

  10.1016/j.crci.2011.02.003

文献信息

• Novel Affinity Ligands for Chromatography Using Combinatorial Chemistry
  作者：Tor Regberg、Charlotta Lindquist、Ake Pilotti、Christel Ellstrom、Lars Fagerstam、Ann Eckersten、Yasuro Shinohara、Steven L. Gallion、Joseph C. Hogan

  DOI：10.2174/138620711795222482

  日期：2011.5.1

  Spatially addressable combinatorial libraries were synthesized by solution phase chemistry and screened for binding to human serum albumin. Members of arylidene diamide libraries were among the best hits found, having submicromolar binding affinities. The results were analyzed by the frequency with which particular substituents appeared among the most potent compounds. After immobilization of the ligands either through the oxazolone or the amine substituent, characterization by surface plasmon resonance showed that ibuprofen affected the binding kinetics, but phenylbutazone did not. It is therefore likely that these compounds bind to Site 2 in sub domain IIIA of human serum albumin (HSA).

  通过溶液相化学合成了空间可寻址的组合库，并对其与人体血清白蛋白的结合能力进行了筛选。在发现的优秀结合分子中，有一类是芳亚基二酰胺类化合物，它们具有亚微摩尔级别的结合亲和力。通过对这些最强效化合物中特定取代基出现的频率进行分析，得出了结果。通过醛酮或胺取代基将配体固定化后，利用表面等离子体共振技术进行表征，结果显示布洛芬影响了结合动力学，而保泰松则没有。因此，这些化合物很可能结合在人血清白蛋白（HSA）亚域IIIA的第2位点上。
• Stereoselective Synthesis of 1,3-Diaminotruxillic Acid Derivatives: An Advantageous Combination of CH-<i>ortho</i> -Palladation and On-Flow [2+2]-Photocycloaddition in Microreactors
  作者：Elena Serrano、Alberto Juan、Angel García-Montero、Tatiana Soler、Francisco Jiménez-Márquez、Carlos Cativiela、M. Victoria Gomez、Esteban P. Urriolabeitia

  DOI：10.1002/chem.201503742

  日期：2016.1.4

  The stereoselective synthesis of ε‐isomers of dimethyl esters of 1,3‐diaminotruxillic acid in three steps is reported. The first step is the ortho‐palladation of (Z)‐2‐aryl‐4‐aryliden‐5(4H)‐oxazolones 1 to give dinuclear complexes 2 with bridging carboxylates. The reaction occurs through regioselective activation of the ortho‐CH bond of the 4‐arylidene ring in carboxylic acids. The second step is

  报道了三步法合成1,3-二氨基苯甲酸的二甲酯的ε-异构体的立体选择性合成。第一步是在邻位的（-palladation Ž）-2-芳基-4- aryliden-5（4 ħ）-oxazolones 1，得到双核配合物2具有桥接羧酸盐。发生该反应通过的区域选择性激活邻-C 在羧酸的4-亚芳基环上的H键。第二个步骤是恶唑酮骨架的环外CC键的在[2 + 2] -photocycloaddition 2，得到相应的双核邻-palladated环丁烷3。通过在流动微反应器中使用具有不同波长（465、525或625 nm）的LED光源，可以非常有效地执行此关键步骤。最后一步涉及在甲醇中加氢使3脱钯，得到单异构体ε-1,3-二氨基truxillicic酸衍生物。
• Sulfanilic Acid-Catalyzed Green Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones
  作者：Hamzeh Kiyani、Shiva Aslanpour

  DOI：10.3987/com-17-13847

  日期：——
• Organic–inorganic hybrid polyoxometalates: Efficient, heterogeneous and reusable catalysts for solvent-free synthesis of azlactones
  作者：Mahbubeh Rostami、Ahmadreza Khosropour、Valiollah Mirkhani、Majid Moghadam、Shahram Tangestaninejad、Iraj Mohammadpoor-Baltork

  DOI：10.1016/j.apcata.2011.02.004

  日期：2011.4

  Two organic-inorganic hybrid polyoxometalates, consist of 1-butyl-3-methylimidazolium salts of (W10O32)(4-) and (RW12O40)(3-) polyanions were prepared and characterized by thermal analysis, X-ray diffraction, FT-IR, diffuse reflectance UV-Vis spectroscopic methods and nitrogen absorption-desorption determination (BET). These heterogeneous catalysts were used for synthesis of azlactones by the reaction of aldehydes with hippuric acid and acetic anhydride under solvent-free conditions. These catalysts were reused several times without loss of their activities. (C) 2011 Elsevier B.V. All rights reserved.
• A simple conversion of azlactones into indenones via H3PW12O40/Al2O3 catalyzed intramolecular Friedel–Crafts reaction
  作者：Mahboubeh Rostami、Ahmad R. Khosropour、Valiollah Mirkhani、Majid Moghadam、Shahram Tangestaninejad、Iraj Mohammadpoor-Baltork

  DOI：10.1016/j.tetlet.2011.10.120

  日期：2011.12

  A rapid and simple procedure for the synthesis of the indenone derivatives, N-(1-oxo-1H-inden-2-yl)benzamides, via intramolecular Friedel-Crafts (IFC) reaction of (Z)-4-arylidene-2-phenyl-5(4)-oxazolones (azlactones) catalyzed by H3PW12O40 supported on neutral alumina under microwave irradiation has been developed. The reaction is straightforward and allows easy isolation of the product. The catalyst could be re-used up to four times after simple filtration. (C) 2011 Elsevier Ltd. All rights reserved.