4-(Z)-(4-(1H-indol-3-yl)methylene)-2-phenyloxazol-4(4H)-one | 42136-84-5

• 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-(Z)-(4-(1H-indol-3-yl)methylene)-2-phenyloxazol-4(4H)-one
• 英文别名: (4Z)-4-((1H-indol-3-yl)methylene)-2-phenyloxazol-5(4H)-one；(4Z)-4-[(1H-indol-3-yl)methylene]-2-phenyloxazol-5(4H)-one；4(Z)-4-((1H-indol-3-yl)methylene)-2-phenyloxazol-5(4H)-one；(Z)-4-((1H-indol-3-yl)methylene)-2-phenyloxazol-5(4H)-one；(Z)-4-[(1H-indol-3-yl)methylene]-2-phenyloxazol-5(4H)-one；(Z)-4-(3-indolylmethylene)-2-phenyl-2-oxazolin-5-one；(4Z)-4-(1H-indol-3-ylmethylidene)-2-phenyl-1,3-oxazol-5-one
• CAS: 42136-84-5；102913-26-8
• 化学式: C₁₈H₁₂N₂O₂
• 分子量: 288.305
• InChiKey: IWPGRLOJSCESNO-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.45
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(Z)-(4-(1H-indol-3-yl)methylene)-2-phenyloxazol-4(4H)-one 在 sodium acetate 、 三乙胺 作用下， 反应 4.0h， 生成 ethyl (Z)-2-benzoylamino-3-(indol-3-yl)acrylate
  参考文献：
  名称：

  Homami, Seyed-Saied; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 6, p. 359 - 361

  摘要：

  DOI：
• 作为产物：
  描述：

  马尿酸 、 3-吲哚甲醛 在 sodium acetate 、 乙酸酐 作用下， 以40%的产率得到4-(Z)-(4-(1H-indol-3-yl)methylene)-2-phenyloxazol-4(4H)-one
  参考文献：
  名称：

  Novel Peptide Mimetic Inhibitors of Hepatitis C Serine Protease Derived from Isomannide

  摘要：

  丙型肝炎病毒感染是导致肝硬化、肝癌或肝功能衰竭等慢性肝病的原因之一，而目前的治疗方法仅对50%的患者有效。HCV中的丝氨酸蛋白酶是最受研究的蛋白酶类别，也是药物开发领域的主要靶点。本文描述了一类新型肽模拟化合物作为潜在HCV丝氨酸蛋白酶抑制剂的合成和生物学研究。

  DOI：

  10.1055/s-0028-1083332

文献信息

• [Et₃NH][HSO₄]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones
  作者：Mehtab Parveen、Faheem Ahmad、Ali Mohammed Malla、Shaista Azaz、Manuela Ramos Silva、P. S. Pereira Silva

  DOI：10.1039/c5ra09290f

  日期：——

  Facile, sustainable and economical synthesis of Erlenmeyer azlactones.

  简便、可持续和经济的合成埃伦迈尔酰胺。
• [C6(MIm)2]2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition
  作者：Mahboubeh Rostami、Ahmad R. Khosropour、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad

  DOI：10.1016/j.crci.2011.02.003

  日期：2011.10

  Résumé Di[1,6-bis(3-methylimidazolium-1-yl)hexane] decatungstate dihydrate ([C6(MIm)2]2W10O32. 2H2O) as a new family of polyoxometalate-based dicationic ionic liquids (POM-DIL) is synthesized and employed as a novel and powerful heterogeneous catalyst in the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones (azlactones) under ultrasound-assisted solvent-free condition. On the basis of the results, the products were obtained in excellent yields under mild condition. Utilization of easy work-up and purification make it very interesting from an economic perspective. Moreover, a recycling study confirmed that the catalyst can be reused multiple times without significant loss of its activity.

  摘要 二水合二[1,6-双(3-甲基咪唑鎓-1-基)己烷]十钨酸[C6(MIm)2]2W10O32·2H2O，作为一类新型多金属氧酸盐基双阳离子离子液体(POM-DIL)，被合成并应用于在超声辅助无溶剂条件下合成4-芳亚甲基-2-苯基-5(4)-噁唑酮(吡唑啉酮)的有效非均相催化剂。基于实验结果，该反应在温和条件下获得了极佳的产率。简便的工作流程和纯化使其在经济角度上具有很高的吸引力。此外，循环利用研究证实了该催化剂可以多次重复使用而不会显著损失其活性。
• Madje, Balaji R.; Ubale, Milind B.; Bharad, Jagdish V., South African Journal of Chemistry, 2010, vol. 63, p. 158 - 161
  作者：Madje, Balaji R.、Ubale, Milind B.、Bharad, Jagdish V.、Shingare, Murlidhar S.

  DOI：——

  日期：——
• Madje, Balaji; Ubale, Milind; Bharad, Jagdish, Journal of the Indian Chemical Society, 2012, vol. 89, # 9, p. 1295 - 1299
  作者：Madje, Balaji、Ubale, Milind、Bharad, Jagdish、Shingare, Murlidhar

  DOI：——

  日期：——
• Organic–inorganic hybrid polyoxometalates: Efficient, heterogeneous and reusable catalysts for solvent-free synthesis of azlactones
  作者：Mahbubeh Rostami、Ahmadreza Khosropour、Valiollah Mirkhani、Majid Moghadam、Shahram Tangestaninejad、Iraj Mohammadpoor-Baltork

  DOI：10.1016/j.apcata.2011.02.004

  日期：2011.4

  Two organic-inorganic hybrid polyoxometalates, consist of 1-butyl-3-methylimidazolium salts of (W10O32)(4-) and (RW12O40)(3-) polyanions were prepared and characterized by thermal analysis, X-ray diffraction, FT-IR, diffuse reflectance UV-Vis spectroscopic methods and nitrogen absorption-desorption determination (BET). These heterogeneous catalysts were used for synthesis of azlactones by the reaction of aldehydes with hippuric acid and acetic anhydride under solvent-free conditions. These catalysts were reused several times without loss of their activities. (C) 2011 Elsevier B.V. All rights reserved.