4-(3,4-Methylenedioxybenzylidene)-2-phenyl-2-imidazolin-5-one | 75793-16-7

• 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: 4-(3,4-Methylenedioxybenzylidene)-2-phenyl-2-imidazolin-5-one
• 英文别名: (4Z)-4-[(2H-1,3-benzodioxol-5-yl)methylidene]-2-phenyl-4,5-dihydro-1H-imidazol-5-one；(Z)-4-((benzo[d][1,3]dioxol-5-yl)methylene)-2-phenyl-1H-imidazol-5(4H)-one；2-phenyl-5-piperonylidene-3,5-dihydro-imidazol-4-one；2-Phenyl-5-piperonyliden-3,5-dihydro-imidazol-4-on；(4Z)-4-(1,3-benzodioxol-5-ylmethylidene)-2-phenyl-4H-imidazol-5-ol；(4Z)-4-(1,3-benzodioxol-5-ylmethylidene)-2-phenyl-1H-imidazol-5-one
• CAS: 75793-16-7
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: ZQUILTIWYULTKI-JYRVWZFOSA-N

物化性质

• 熔点：
  303-304 °C(Solv: isobutanol (78-83-1))
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,4-Methylenedioxybenzylidene)-2-phenyl-2-imidazolin-5-one 在 氢氧化钾 、 锌 作用下， 反应 1.0h， 以50%的产率得到N-benzoyl-3,4-methylenedioxy-DL-phenylalanine
  参考文献：
  名称：

  Devasia, Ganapathiplackal M.; Shafi, P. Mohamed, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 204 - 206

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2-phenyl-4-piperonylidene-2-oxazoline-5(4H)-one 在 尿素 作用下， 以 乙二醇 为溶剂， 反应 0.07h， 以85%的产率得到4-(3,4-Methylenedioxybenzylidene)-2-phenyl-2-imidazolin-5-one
  参考文献：
  名称：

  Efficient microwave-assisted synthesis and antioxidant activity of 4-arylidene-2-phenyl-1H-imidazol-5(4H)-ones

  摘要：

  AbstractThe efficient synthesis of 4‐arylidene‐2‐phenyl‐1H‐imidazol‐5(4H)‐ones was achieved via microwave‐assisted reactions of 4‐arylmethylene‐2‐phenyloxazol‐5(4H)‐ones with urea in glycol. This approach provides a facile shortcut for the synthesis of this type of compounds with short reaction time, high yields, broad substrate scope and easy operation. Besides, the synthesized compounds were subject to the test of antioxidant activity, which is represented by their capacities for scavenging 1,1‐diphenyl‐2‐picrylhydrazyl, hydroxyl and superoxide anion free radicals. Bioassay of these compounds resulted in the finding of several 4‐arylidene‐2‐phenyl‐1H‐imidazol‐5(4H)‐ones with significant antioxidant activity. J. Heterocyclic Chem., (2012).

  DOI：

  10.1002/jhet.766

文献信息

• Devasia, Ganapathiplackal M.; Shafi, P. Mohamed, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 8, p. 657 - 660
  作者：Devasia, Ganapathiplackal M.、Shafi, P. Mohamed

  DOI：——

  日期：——
• Some Reaction Products of Aromatic Amidines with Diketones, Dialdehydes and their Monoximes
  作者：John B. Ekeley、J. Lell Elliott

  DOI：10.1021/ja01292a047

  日期：1936.1
• DEVASIA G. M.; SHAFI P. MOHAMED, INDIAN J. CHEM., 1979, B 17, NO 5, 526-527
  作者：DEVASIA G. M.、 SHAFI P. MOHAMED

  DOI：——

  日期：——
• DEVASIA, GANAPATHIPLACKAL, M.;SHAFI, P. MOHAMED, INDIAN J. CHEM., 1981, 20, N 8, 657-660
  作者：DEVASIA, GANAPATHIPLACKAL, M.、SHAFI, P. MOHAMED

  DOI：——

  日期：——
• Efficient microwave-assisted synthesis and antioxidant activity of 4-arylidene-2-phenyl-1H-imidazol-5(4H)-ones
  作者：Feng Shi、Xiao-Ning Zeng、Fei-Yue Wu、Shu Yan、Wei-Fa Zheng、Shu-Jiang Tu

  DOI：10.1002/jhet.766

  日期：2012.1

  AbstractThe efficient synthesis of 4‐arylidene‐2‐phenyl‐1H‐imidazol‐5(4H)‐ones was achieved via microwave‐assisted reactions of 4‐arylmethylene‐2‐phenyloxazol‐5(4H)‐ones with urea in glycol. This approach provides a facile shortcut for the synthesis of this type of compounds with short reaction time, high yields, broad substrate scope and easy operation. Besides, the synthesized compounds were subject to the test of antioxidant activity, which is represented by their capacities for scavenging 1,1‐diphenyl‐2‐picrylhydrazyl, hydroxyl and superoxide anion free radicals. Bioassay of these compounds resulted in the finding of several 4‐arylidene‐2‐phenyl‐1H‐imidazol‐5(4H)‐ones with significant antioxidant activity. J. Heterocyclic Chem., (2012).