(4Z,4'Z)-4,4'-(1,4-phenylenebis(methanylylidene))bis(2-phenyloxazol-5(4H)-one) | 1283716-01-7

• 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: (4Z,4'Z)-4,4'-(1,4-phenylenebis(methanylylidene))bis(2-phenyloxazol-5(4H)-one)
• 英文别名: (4Z)-4-[[4-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenyl]methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 1283716-01-7
• 化学式: C₂₆H₁₆N₂O₄
• 分子量: 420.424
• InChiKey: XYSKEVMXUOWHBI-BMJUYKDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4Z,4'Z)-4,4'-(1,4-phenylenebis(methanylylidene))bis(2-phenyloxazol-5(4H)-one) 反应 0.7h， 以80%的产率得到N,N'-(1,5-dioxo-1,5-dihydro-s-indacene-2,6-diyl)dibenzamide
  参考文献：
  名称：

  A simple conversion of azlactones into indenones via H3PW12O40/Al2O3 catalyzed intramolecular Friedel–Crafts reaction

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.10.120
• 作为产物：
  描述：

  马尿酸 、 对苯二甲醛 在 乙酸酐 作用下， 反应 0.37h， 以88%的产率得到(4Z,4'Z)-4,4'-(1,4-phenylenebis(methanylylidene))bis(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 and chemoselective one-pot synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones starting from benzyl alcohols promoted by [(C14H24N4)2W10O32]-[bmim]NO3
  作者：Mahboubeh Rostami、Ahmad Reza Khosropour、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad

  DOI：10.1007/s00706-011-0533-3

  日期：2011.11

  AbstractA new and practical promoter system for one-pot, efficient, chemoselective synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones using [(C14H24N4)2W10O32]-[bmim]NO3 under solvent-free conditions is described. The present work opens up a new and ecofriendly synthetic route to Erlenmeyer–Plöchl adducts from primary benzyl alcohols in a one-pot operation. Graphical abstract

  摘要一种新型实用的促进剂体系，可使用[（C 14 H 24 N 4）2 W 10 O 32 ]-[bmim进行一锅高效化学选择合成4-亚芳基-2-苯基-5（4 H）-恶唑酮描述了在无溶剂条件下的] NO 3。目前的工作为一锅操作从伯苄醇到Erlenmeyer-Plöchl加合物的合成开辟了一条新的环保途径。 图形概要
• An innovation for development of Erlenmeyer–Plöchl reaction and synthesis of AT-130 analogous: a new application of continuous-flow method
  作者：Behnaz Shafiee、Laleh Hadian、Ahmad R. Khosropour

  DOI：10.1039/c6ra00301j

  日期：——

  and efficient processes via one-pot multicomponent synthesis is a very attractive topic. In this work, the Erlenmeyer–Plöchl azlactone synthesis was carried out through unique, safe, fast and practical conditions without any catalyst, applying a simple microreactor and gave the corresponding products exclusively. A continuous, first microflow synthesis of N-benzoylglycine carbamide derivatives as AT-130

  通过一锅多组分合成技术开发环保，高效的方法是一个非常有吸引力的话题。在这项工作中，Erlenmeyer–Plöchl z内酯的合成是通过独特，安全，快速和实用的条件进行的，无需任何催化剂，使用简单的微反应器，即可得到相应的产物。还成功建立了Nafion-H @ SPIONs催化的连续首次微流合成N-苯甲酰基甘氨酸氨基甲酰胺衍生物作为AT-130类似物的方法。
• An eco-compatible access to diversified bisoxazolone and bisimidazole derivatives
  作者：Wael Abdelgayed Ahmed Arafa、Ahmed Fawzy Abdel-Magied

  DOI：10.24820/ark.5550190.p010.544

  日期：——

  An efficient, straight-forward and eco-friendly synthetic strategy for the assembly of novel bisoxazolones via a four-component, sequential reaction of dialdehydes, glycine, benzoyl chloride and ac ...

  通过二醛、甘氨酸、苯甲酰氯和 ac 的四组分顺序反应组装新型双恶唑酮的高效、直接和环保的合成策略
• Unsaturated 4,4′-bis-[5(4H)-oxazolones]: Synthesis and evaluation of their ortho-palladation through C–H bond activation
  作者：Gheorghe-Doru Roiban、Tatiana Soler、Ion Grosu、Carlos Cativiela、Esteban P. Urriolabeitia

  DOI：10.1016/j.ica.2010.12.054

  日期：2011.3

  Aromatic unsaturated 4,4′-bis-[5(4H)-oxazolones] have been prepared and their structural properties discussed. Metallation studies of these substrates towards palladium(II) acetate were also investigated.

  制备了芳香族不饱和4,4'-双-[5（4 H）-恶唑酮]，并对其结构性质进行了讨论。还研究了这些基材对乙酸钯（II）的金属化研究。
• CsF-Catalyzed Transannulation Reaction of Oxazolones: Diastereoselective Synthesis of Diversified <i>trans</i>-<i>N</i>-(6-Oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with Arylidene Azlactones and Amidines
  作者：Golnaz Parhizkar、Ahmad Reza Khosropour、Iraj Mohammadpoor-Baltork、Elahehnaz Parhizkar、Hadi Amiri Rudbari

  DOI：10.1021/acscombsci.8b00027

  日期：2018.6.11

  straightforward synthetic strategy for the construction of new tetrasubstituted 1,3-diazinones is described. The procedure is based on CsF-catalyzed, microwave-assisted, ring transformation reaction of arylidene azlactones with amidines. Moreover, this technique provides diversified trans-N-(6-oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with a good antimicrobial activity.

  描述了一种用于构建新的四取代的1，3-二氮杂二酮的通用且直接的合成策略。该程序基于CsF催化的亚芳基a内酯与am的微波辅助环转化反应。此外，该技术提供了多元化反式- ñ - （6-氧代-1,4,5,6-四氢嘧啶-5-基）具有良好的抗微生物活性的苯甲酰胺。