2-phenyl-4-(2-furylmethylidene)-2-oxazolin-5-one | 77012-48-7

• 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: 2-phenyl-4-(2-furylmethylidene)-2-oxazolin-5-one
• 英文别名: 4-((furan-2-yl)methylene)-2-phenyloxazol-5(4H)-one；4-[(Furan-2-yl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one；4-(furan-2-ylmethylidene)-2-phenyl-1,3-oxazol-5-one
• CAS: 77012-48-7
• 化学式: C₁₄H₉NO₃
• mdl: MFCD00159522
• 分子量: 239.23
• InChiKey: QJBMVCDGBSYRJD-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  360.3±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(2-furylmethylidene)-2-oxazolin-5-one 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以72%的产率得到2-(furfuryl)-2-benzamidoethylamine
  参考文献：
  名称：

  Kidwai, Journal of the Indian Chemical Society, 1990, vol. 67, # 6, p. 470 - 471

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 在 氢氧化钾 、 sodium hydroxide 作用下， 反应 12.0h， 生成 2-phenyl-4-(2-furylmethylidene)-2-oxazolin-5-one
  参考文献：
  名称：

  THE PREPARATION OF 1-(2-FURYL)-2-AMINO-1,3-PROPANEDIOL AND DERIVATIVES

  摘要：

  DOI：

  10.1021/jo01142a017

文献信息

• Greener approach: Ionic liquid [Et₃NH][HSO₄]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4<i>H</i>)oxazolones under solvent-free condition
  作者：Santosh A. Jadhav、Aniket P. Sarkate、Mazahar Farooqui、Devanand B. Shinde

  DOI：10.1080/00397911.2017.1340649

  日期：2017.9.17

  chloride, amino acid, and a variety of aldehydes catalyzed by ILs [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate. The final products were confirmed by their characterization data such as FTIR, 1H-NMR, 13C-NMR, Mass, high-resolution mass spectra and were compared with its reported method. GRAPHICAL ABSTRACT

  摘要 我们开发了简单、更环保、更安全的多组分合成系列 4-亚芳基-2-苯基-5(4H) 恶唑酮 4(ar) 以三乙基硫酸氢铵 [Et3NH][HSO4] 为催化的布朗斯台德酸离子液体和催化量的乙酸酐和乙酸钠，产率极好（90-99%）。该协议提供了经济、环境友好、无溶剂的条件，以及催化剂的回收再利用，并且从苯甲酰氯 1、氨基酸 2 和各种醛 3 开始很容易获得。 环化后苯甲酰氯、氨基酸的缩合，以及由ILs [Et3NH][HSO4]和催化量的乙酸酐和乙酸钠催化的多种醛。最终产物通过其表征数据如 FTIR、1H-NMR、13C-NMR、Mass、高分辨率质谱，并与其报道的方法进行了比较。图形概要
• A simple and efficient method for the synthesis of Erlenmeyer azlactones
  作者：Philip A. Conway、Kevin Devine、Francesca Paradisi

  DOI：10.1016/j.tet.2009.02.011

  日期：2009.4

  novel and efficient method for synthesising Erlenmeyer azlactones under mild and rapid conditions. The reaction is performed by reacting 2-phenyl-5-oxazolone with an aldehyde in dichloromethane using alumina as a catalyst. The materials react instantly at room temperature, negating the need for high temperatures and long reaction times. We have successfully used this method for both aliphatic, aromatic

  我们最近开发了一种新颖，有效的方法，可在温和快速的条件下合成锥形戊二酸内酯。通过使用氧化铝作为催化剂，使2-苯基-5-恶唑酮与醛在二氯甲烷中反应来进行反应。该材料在室温下可立即反应，从而无需高温和较长的反应时间。我们已经成功地将这种方法用于脂肪族，芳香族和杂芳香族醛类，以中等至高产率合成了以前未制得的锥形戊二烯酮。
• Synthesis and Herbicidal Activity of 4-Benzylidene-2-phenyl oxazol-5(4H)-one Derivatives using L-Proline as Catalyst
  作者：S. Bhandari、V. Kasana

  DOI：10.14233/ajchem.2018.21251

  日期：——

  A simple, efficient and environmentally benign method for the synthesis of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives by the reaction of aromatic aldehydes and hippuric acid using acetic anhydride as dehydrating agent and L-proline as catalyst has been developed. L-proline acts as a highly efficient organocatalyst. It is thermally stable and can withstand harsh reaction conditions besides being easily available and environmentally non-hazardous. The structures of synthesized compounds were evaluated by FT-IR and 1H-NMR spectroscopy. The present method is superior to the existing methods as it takes less reaction time, involves easy work up and affords products in excellent yield. The preliminary bioassay of synthesized compounds indicated that most of the compounds exhibited good seed germination inhibition activity against radish seed (Raphanus sativus).

  开发了一种简单、高效且环保的方法，通过芳香醛和水杨酸在醋酸酐作为脱水剂和L-脯氨酸作为催化剂的作用下合成4-苯甲叉-2-苯基噁唑-5(4H)-酮衍生物。L-脯氨酸作为一种高效的有机催化剂，具有热稳定性，能够耐受苛刻的反应条件，且易于获得且环境友好。合成化合物的结构通过FT-IR和1H-NMR光谱进行了评估。该方法优于现有方法，因为它反应时间更短，操作简便，并且产物收率极高。合成化合物的初步生物测定表明，大多数化合物对拟南芥种子（Raphanus sativus）表现出良好的种子发芽抑制活性。
• Sonochemical Hot-spot Assisted One-pot Synthesis of 4-arylmethylidene - 2-phenyl-4H-oxazol-5-ones Using Nano-MgO as an Efficient Catalyst
  作者：Sadeq Hamood Saleh Azzam、G. T. Chandrappa、Mohamed Afzal Pasha

  DOI：10.2174/1570178611310040010

  日期：2013.5.1

  Twelve 4-arylmethylidene-2-phenyl-4H-oxazol-5-ones were prepared in excellent yield by sonicating a mixture of an araldehyde, hippuric acid and acetic anhydride in the presence of a green heterogeneous NanoMgO as a basic catalyst. The catalytic activity of NanoMgO was found to be higher compared with bulk MgO powder under the same conditions. This method provides several advantages such as short reaction time, high yields, cleaner reaction condition, involves simple and easy workup procedure makes this protocol economically viable.

  十二种4-芳基亚甲基-2-苯基-4H-噁唑-5-酮在超声波作用下，通过将芳醛、氨基苯甲酸和醋酸酐的混合物与绿色的非均相NanoMgO作为碱催化剂反应，以优异的产率制备而成。在相同条件下，NanoMgO的催化活性高于块状MgO粉末。该方法具有多个优点，如反应时间短、产率高、反应条件更干净，以及操作简单易行，使得该方案在经济上可行。
• 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。