4-(3'-phenyl-2'-propenylidene)-2-phenyloxazol-5(4H)-one | 21366-59-6

• 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: 4-(3'-phenyl-2'-propenylidene)-2-phenyloxazol-5(4H)-one
• 英文别名: (Z)-4-cinnamylidene-2-phenyl-2-oxazolin-5-one；2-phenyl-4-styrylmethylene-2-oxazolin-5-one；2-phenyl-4-(3-phenyl-allylidene)-4H-oxazol-5-one；4-seqcis-2-Phenyl-4-(3-phenyl-propen-(2)-yliden)-2-oxazolinon-(5)
• CAS: 21366-59-6
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: AYHSMADDXZUZBX-VQDJSFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(3'-phenyl-2'-propenylidene)-2-phenyloxazol-5(4H)-one 在 氢氧化钾 、 三乙胺 作用下， 生成 (2Z,4E)-2-Benzoylamino-5-phenyl-penta-2,4-dienoic acid
  参考文献：
  名称：

  Joseph, Kiran; Chowdary, Y Rekha; Mukerjee, Arya K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 4, p. 230 - 232

  摘要：

  DOI：
• 作为产物：
  描述：

  (2Z,4E)-2-Benzoylamino-5-phenyl-penta-2,4-dienoic acid 在 氯甲酸乙酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 15.0h， 以82%的产率得到4-(3'-phenyl-2'-propenylidene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  A Fast Synthesis of 2-Acylamino-2-alkenoic Acids

  摘要：

  DOI：

  10.1055/s-1984-30859

文献信息

• Study on dry-media microwave azalactone synthesis on different supported KF catalysts: influence of textural and acid–base properties of supports
  作者：Felipa M. Bautista、Juan M. Campelo、Angel García、Diego Luna、José M. Marinas、Antonio A. Romero

  DOI：10.1039/b109413k

  日期：2002.1.23

  Twenty-five inorganic solids studied as supports for KF were screened with respect to the synthesis of the azalactone obtained by dry-media condensation of p-hydroxybenzaldehyde with hippuric acid in acetic anhydride (1 ∶ 1 ∶ 4, molar ratio), in 3 g of 10 wt% KF support catalysts. The results obtained indicate that there was a number of supported KF catalysts with conversions higher than or comparable to that obtained by the classical Erlenmeyer method of azalactone synthesis. Furthermore, not only were there very important differences in the catalytic behavior of different KF support systems, but also these differences are closely related to the procedure used in the reaction heating. In this respect, the well-documented KF–Al2O3 was the best catalyst when reactions were conducted under conventional heating. However, when reactions were carried out in a domestic microwave oven, KF supported on AlPO4, TiO2 or Zn3(PO4)2 were better catalysts than KF–Al2O3. The importance of the textural and acid–base properties of solid inorganic supports was also demonstrated with respect to the catalytic behavior of supported KF catalysts. Finally, results obtained in the synthesis of thirteen different azalactones, lead us strongly to recommend the procedure using microwave irradiation and KF–AlPO4, over classical heating with KF–Al2O3. The advantages are good yields, easier work-up, a significant decrease in reaction times, and easy re-use of catalysts when operated in dry-media, especially by use of a domestic microwave oven.

  筛选了25种无机固体作为KF的载体，研究了它们在醋酸酐中与对羟基苯甲醛和马尿酸进行干介质缩合合成的Azalactone的效率（1 : 1 : 4的摩尔比），采用3克的10 wt% KF载体催化剂。结果表明，存在一些KF载体催化剂的转化率高于或媲美经典的Erlenmeyer法合成Azalactone的转化率。此外，不同KF载体系统的催化行为存在非常重要的差异，这些差异与反应加热的程序密切相关。在这方面，经过充分文献证明的KF–Al2O3在常规加热下的反应中是最佳催化剂。然而，当反应在家庭微波炉中进行时，载于AlPO4、TiO2或Zn3(PO4)2上的KF表现出优于KF–Al2O3的催化活性。固体无机载体的纹理和酸碱特性对支持KF催化剂的催化行为的重要性也得到了验证。最后，在合成十三种不同的Azalactone的研究结果使我们强烈推荐在微波辐射条件下使用KF–AlPO4的程序，而不是使用KF–Al2O3的经典加热方法。其优势在于产率良好、处理更简便、反应时间显著缩短，以及在干介质下操作时催化剂的易于重复使用，尤其是使用家庭微波炉时。
• Structure-Activity Design, Synthesis and Biological Activity of Newer Imidazole- Triazine Clubbed Derivatives as Antimicrobial and Antitubercular Agents
  作者：Jaydeep A. Patel、Navin B. Patel、Pratik K. Maisuriya、Monika R. Tiwari、Amit C. Purohit

  DOI：10.2174/1570178618666210521150011

  日期：2022.2

  PLSR method is applied for 2D-QSAR determination of the (Z)-5-ethylidene-3-(4- methoxy-6-methyl-1,3,5-triazin-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-one (B1-B10). The designed compounds were synthesized and spectrally evicted by IR, 1H NMR, 13C NMR, and mass spectra data as well as biologically screened against the different antitubercular and antimicrobial species.

  方法：应用PLSR方法对（Z）-5-乙烯基-3-（4-甲氧基-6-甲基-1,3,5-三唑-2-基）-2-苯基-3,5-二氢-4H-咪唑-4-酮（B1-B10）的二维定量构效关系（2D-QSAR）进行确定。设计的化合物经合成，并通过红外光谱、1H核磁共振、13C核磁共振和质谱数据进行光谱验证，同时对其进行了不同抗结核和抗微生物物种的生物筛选。
• Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl-5(4 H )-oxazolones under solvent-free conditions
  作者：Satya Paul、Puja Nanda、Rajive Gupta、André Loupy

  DOI：10.1016/j.tetlet.2003.10.125

  日期：2004.1

  Eight 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) have been prepared via Erlenmeyer synthesis from aromatic aldehydes and hippuric acid using calcium acetate under solvent-free conditions with microwave irradiation. (C) 2003 Elsevier Ltd. All rights reserved.
• Hirpara; Parikh; Merja, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 5, p. 1172 - 1175
  作者：Hirpara、Parikh、Merja、Parekh

  DOI：——

  日期：——
• A Facile Synthesis of<i>N</i>-Substituted 2-Acylamino-2-alkenamides
  作者：Pradeep K. Tripathy、Arya K. Mukerjee

  DOI：10.1055/s-1985-31179

  日期：——