4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
• 英文别名: 2-phenyl-4-(vanillylidene)-2-oxazolin-5-one；2-phenyl-4-(3-methoxy, 4-hydroxy arylidene)-1,3-oxazol-5-one；4-(4-hydroxy-3-methoxy)benzylidene-2-phenyloxazol-5-one；4-(4-hydroxy-3-methoxy-benzylidene)-2-phenyl-4H-oxazol-5-one；4-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: QFFUNXWMPNHGMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone 在 sodium acetate 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 1,2-Diphenyl-4-(4-ethoxycarbonyloxy-3-methoxybenzylidene)-Δ²-imidazolin-5-one
  参考文献：
  名称：

  Kumar, Pradeep; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 5, p. 416 - 418

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 在 potassium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 生成 4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
  参考文献：
  名称：

  新型非核苷HIV-1逆转录酶抑制剂咪唑-5-酮的合成，生物学活性和对接研究

  摘要：

  设计，合成了一系列新的取代的咪唑-5-酮，并使用逆转录酶测定试剂盒（Roche，Colorimetric）评估了其在体外的逆转录酶（RT）抑制活性。从体外筛选观察到，新合成的化合物具有RT抑制活性。进行对接研究以研究合成化合物对RT酶的结合方向和亲和力。

  DOI：

  10.1016/j.bmc.2012.02.037

文献信息

• Design, Synthesis, and Antimicrobial Activity of Novel Fluorine-Containing Imidazolones
  作者：N. C. Desai、K. R. Wadekar、H. K. Mehta、U. P. Pandit

  DOI：10.1134/s1070428021060142

  日期：2021.6

  Abstract A simple synthetic protocol have been developed for the preparation of novel N-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N′-phenylthiourea derivatives by the reaction of 4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones with N-(3-chloro-4-fluorophenyl)- and N-[3-(trifluoromethyl)phenyl)hydrazinecarbothioamides. The synthesized imidazolones have been characterized by using

  摘要 一个简单的合成方案已被开发用于新颖的制备ñ - （4-苯亚甲基-5-氧代-2-苯基-4,5-二氢-1- ħ -咪唑-1-基）ñ由'-phenylthiourea衍生物4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones 与N- (3-chloro-4-fluorophenyl)- 和N- [3-(trifluoromethyl)phenyl)hydrazinecarbothioamides 的反应. 合成的咪唑酮已通过使用不同的光谱技术进行表征，并评估了它们对某些细菌和真菌菌株的抗菌活性。发现含有 2-硝基亚苄基和 4-甲氧基亚苄基取代基的咪唑酮衍生物对真菌菌株白色念珠菌和棒状曲霉..
• Efficient Synthesis of 5(4H)-Imidazolones and in vitro Antifungal Activity Studies Against Selected Phytopathogens
  作者：Christopher Voosala、Lakshmi Narasimha Murthy Yellajyosula、Viplava Prasad Uppuleti、Padma Suhasini Kilaru

  DOI：10.14233/ajchem.2014.15893

  日期：——

  A series of five new 1-(substituted phenyl)-2-phenyl-4-(substituted benzylidine)imidazole-5-one derivatives (or) 5(4H)-imidazolones have been synthesized adopting SiO2, Al2O3-90 and Y-faujasite (Y-H type) zeolite as catalysts. These compounds were assayed for their antifungal activity on three different selected phytopathogens which disparately affects the Jowar crop (Sorghum vulgare) of poaceae family. Among the screened target molecules, compound 18 exhibited potent inhibitory activity compared to the standard drug bavistine, which is worth for further investigation.

  一系列五个新的1-（取代苯基）-2-苯基-4-（取代苯亚甲基）咪唑-5-酮（或）5（4H）-咪唑酮通过采用SiO2、Al2O3-90和Y型丝光沸石（Y-H型）作为催化剂合成。这些化合物对选定的三种不同影响高粱（禾本科的Sorghum vulgare）的植物病原体进行了抗真菌活性测试。在筛选的目标分子中，化合物18显示出比标准药物巴维菌素更强的抑制活性，值得进一步研究。
• A Facile and Efficient Synthesis of 4-Arylidene-2-phenyl-5(4<i>H</i>)-oxazolones and Their Antimicrobial Evaluation against Selected Human and Phytopathogens
  作者：Christopher Voosala、Padma Suhasini Kilaru、Uday Kumar Dasari

  DOI：10.1002/jccs.201600083

  日期：2016.11

  series of 2‐(4‐substituted phenyl)‐4‐(substituted arylidene)‐1,3‐oxazol‐5‐ones (5a–j) via reactions of hippuric acid with differently substituted aromatic aldehydes (4a–j) in sodium acetate, potassium acetate, calcium acetate, and ammonium acetate, respectively, which were tested for their efficiency as catalysts in both conventional and microwave‐assisted synthetic methods in presence of 4 Å zeolites

  已经开发了一种简单方便的方法，用于通过马尿酸的反应合成一系列2-（4-取代的苯基）-4-（取代的亚芳基）-1,3-恶唑-5-（5a–j）。分别在乙酸钠，乙酸钾，乙酸钙和乙酸铵中分别使用不同取代的芳族醛（4a–j），测试了它们在4沸石存在下作为常规方法和微波辅助合成方法作为催化剂的效率。评价了标题化合物对选定的人类病原体（细菌和真菌）和植物病原体（真菌）的抗菌性能，并与标准药物进行了比较。报告了研究结果。
• Synthesis, Characterization and Biological Activity of 5-Arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4<i>H</i>-imidazol-4-ones
  作者：B. B. Baldaniya

  DOI：10.1155/2010/264036

  日期：——

  Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q)have been synthesized and characterized by elemental analyses, IR, NMR, and mass spectra. The products have been evaluated for antibacterial and antifungal activities against different strains of bacteria and fungi.

  一些新型的5-芳基亚醛基-3-(6,7-二氯-1,3-苯并噻唑-2-基)-2-苯基-3,5-二氢-4H-咪唑-4-酮 (6a-q)已经合成并通过元素分析、红外光谱、核磁共振和质谱进行了表征。这些产物已经针对不同菌株的细菌和真菌进行了抗菌和抗真菌活性评价。
• One-pot process to Z-α-benzoylamino-acrylic acid methyl esters via potassium phosphate-catalyzed Erlenmeyer reaction
  作者：Thomas Cleary、Jodie Brice、Nicole Kennedy、Flavio Chavez

  DOI：10.1016/j.tetlet.2009.11.081

  日期：2010.1

  A practical and efficient two reaction sequence one-pot process for the synthesis of Z-α-benzoylamino-acrylic acid methyl esters was developed. The process involves a potassium phosphate-catalyzed Erlenmeyer reaction of aromatic aldehydes with hippuric acid followed by an oxazolone ring-opening methanolysis. This process afforded a good overall yield and an excellent product quality via a simple workup

  提出了一种实用，高效的二反应一锅法合成Z -α-苯甲酰氨基丙烯酸丙烯酸甲酯的方法。该方法涉及芳族醛与马尿酸的磷酸钾催化的埃伦迈耶反应，然后进行恶唑酮开环甲醇分解反应。通过简单的后处理，该过程提供了良好的总产量和优异的产品质量。