4-[(2-Ethoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one | 328548-32-9

• 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-[(2-Ethoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 328548-32-9
• 化学式: C₁₈H₁₅NO₃
• mdl: MFCD00178388
• 分子量: 293.322
• InChiKey: GLWZPSWAYVIILY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙氧基苯甲醛 、 N-乙酰甘氨酸 在 zinc(II) oxide 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以70%的产率得到4-[(2-Ethoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and pharmacological evaluation of oxazolone derivatives

  摘要：

  一系列 4-芳基亚甲基-2-苯基/甲基-5-(4H)-恶唑酮衍生物 (2-7) (2-7) 的合成采用了已报道的方法。 醛与 N-苯甲酰基/N-乙酰基甘氨酸在氧化锌作为催化剂和乙酸酐存在下缩合合成了 催化剂和乙酸酐的作用下，在乙醇中于室温缩合醛与 N-苯甲酰基/N-乙酰基甘氨酸。这些化合物 (2-6）是新的衍生物。根据 1H-NMR 根据 1H-NMR、13C-NMR、EIMS、FT-IR 和元素分析对化合物的结构进行了评估。对所有 化合物的抗菌和抑制脲酶活性进行了筛选。 活性。抗菌活性测试采用琼脂井扩散法 抗菌活性。化合物 (2) 对金黄色葡萄球菌的抑制率为 16 毫米（80%），对伤寒杆菌的抑制率超过 24 毫米（70%）。 对伤寒杆菌的抑制率超过 24 毫米（70%）。对大肠杆菌最有效的化合物是化合物 (6) 其次是化合物 (5)，抑制率超过 18 毫米（80%）。 （70%）。所有化合物的尿素酶抑制活性都是通过靛酚法测定的。 靛酚法测定。化合物（3、6）和（7）对蚕豆尿素酶有明显的抑制作用。 对积雪豆脲酶有明显的抑制作用。

  DOI：

  10.2298/jsc120917126f

文献信息

• Khan, Saadia Razi; Ghouri, Nida; Karim, Aneela, Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 5, p. 980 - 985
  作者：Khan, Saadia Razi、Ghouri, Nida、Karim, Aneela、Naz, Farzana、Fakhri, Muhammad Imran、Perveen, Shahnaz、Khan, Khalid Mohammed、Taha, Muhammad、Choudhary, Muhammad Iqbal

  DOI：——

  日期：——
• Ortho-Palladation of (<i>Z</i>)-2-Aryl-4-Arylidene-5(4<i>H</i>)-Oxazolones. Structure and Functionalization
  作者：Gheorghe-Doru Roiban、Elena Serrano、Tatiana Soler、Maria Contel、Ion Grosu、Carlos Cativiela、Esteban P. Urriolabeitia

  DOI：10.1021/om901068f

  日期：2010.3.22

  Ortho-palladated complexes of (Z)-2-aryl-4-arylidene-5(4H)-oxazolones have been prepared through oxidative addition. The reaction of (Z)-2-phenyl-4-(2-bromobenzylidene)-5(4H)-oxazolone (4) with Pd-2(dba)(3)center dot CHCl3 gives the six-membered cyclopalladated dinuclear complex [Pd(mu-Br)(o-C6H4CH=CNC(O)OCPh)](2) (7). The reaction of 7 with PPh3 gives dinuclear 9, which incorporates one phosphine per Pd atom through cleavage of the Pd-N bond, and preserves the bromide bridging system. However, reaction with PPh2Me gives mononuclear 8, which incorporates two phosphines as a results of the cleavage of the mu-Br system and N displacement. In contrast, the reaction of 7 with pyridine gives complex 12 due to Simple cleavage of the Br bridge, leaving the N-bonding intact. Therefore, three different reaction pathways have been characterized. The reactivity of the Pd-C bond in 7 has also been examined, and functionalized oxazolones can be obtained. The reaction of 7 With PhI(OAc)(2) in acetic acid gives the starting oxazolone C6H4-2-Br-CH=CNC(O)OCPh (4), through the presumed oxidation of the Pd center and C-Br bond formation by reductive coupling. In contrast, the reaction of the acetate dimer 14 with PhI(OAc)(2) in acetic acid gives C6H4-2-OAc-CH=CNC(O)OCPh (20) through C-O coupling. When treatment of 7 with PhI(OAc)(2) is performed in MeOH or EtOH, the oxazolones C6H4-2-OR-CH=CNC(O)OCPh (R = Me (18), Et (19)) are obtained. The reaction of 7 with CO in alcohols ROH gives cleanly the oxazolones C6H4-2-CO2R-CH=CNC(O)OCPh (R = Me (21), Pr-i (22)) through CO migratory insertion into the Pd-C bond and further nucleophilic attack of the RO- fragment.
• Synthesis, spectroscopic characterization and pharmacological evaluation of oxazolone derivatives
  作者：Ghulam Fareed、Nighat Afza、Ali Versiani、Nazia Fareed、Rasheed Mughal、Ali Kalhoro、Lubna Iqbal、Mehreen Lateef

  DOI：10.2298/jsc120917126f

  日期：——

  A series of 4-aryl methylidene-2-phenyl/methyl-5-(4H)-oxazolone derivatives (2-7) have been synthesized using the reported method by condensation of aldehydes with N-benzoyl / N-acetyl glycine in the presence of zinc oxide as a catalyst and acetic anhydride at room temperature in ethanol. The compounds (2-6) are new derivatives. The structures of compounds were evaluated on the basis of 1H-NMR, 13C-NMR, EIMS, FT-IR and elemental analysis. All the compounds were screened for their antibacterial and urease inhibition activity. Antibacterial activity was tested by agar well diffusion method using Mueller Hinton Agar medium. Compound (2) showed excellent activity against S. aureus which has 16 mm (80%) inhibition and above 24 mm (70%) against S. typhi. The most active compound against E. coli was compound (6) having 20 mm (80%) inhibition followed by compound (5) having above 18 mm (70%) inhibition. Urease inhibition activity of all the compounds was determined by indophenol method. Compounds (3, 6) and (7) showed significant inhibition against Jacks bean urease.

  一系列 4-芳基亚甲基-2-苯基/甲基-5-(4H)-恶唑酮衍生物 (2-7) (2-7) 的合成采用了已报道的方法。 醛与 N-苯甲酰基/N-乙酰基甘氨酸在氧化锌作为催化剂和乙酸酐存在下缩合合成了 催化剂和乙酸酐的作用下，在乙醇中于室温缩合醛与 N-苯甲酰基/N-乙酰基甘氨酸。这些化合物 (2-6）是新的衍生物。根据 1H-NMR 根据 1H-NMR、13C-NMR、EIMS、FT-IR 和元素分析对化合物的结构进行了评估。对所有 化合物的抗菌和抑制脲酶活性进行了筛选。 活性。抗菌活性测试采用琼脂井扩散法 抗菌活性。化合物 (2) 对金黄色葡萄球菌的抑制率为 16 毫米（80%），对伤寒杆菌的抑制率超过 24 毫米（70%）。 对伤寒杆菌的抑制率超过 24 毫米（70%）。对大肠杆菌最有效的化合物是化合物 (6) 其次是化合物 (5)，抑制率超过 18 毫米（80%）。 （70%）。所有化合物的尿素酶抑制活性都是通过靛酚法测定的。 靛酚法测定。化合物（3、6）和（7）对蚕豆尿素酶有明显的抑制作用。 对积雪豆脲酶有明显的抑制作用。