4-(3-bromobenzylidene)-2-phenyloxazol-5(4H)-one | 312734-88-6

• 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-bromobenzylidene)-2-phenyloxazol-5(4H)-one
• 英文别名: 4-[(3-Bromophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 312734-88-6
• 化学式: C₁₆H₁₀BrNO₂
• mdl: MFCD00176210
• 分子量: 328.165
• InChiKey: LVBYPCCDULQAKE-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  435.4±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-bromobenzylidene)-2-phenyloxazol-5(4H)-one 反应 0.67h， 以85%的产率得到N-(7-bromo-1-oxoinden-2-yl)benzamide
  参考文献：
  名称：

  A simple conversion of azlactones into indenones via H3PW12O40/Al2O3 catalyzed intramolecular Friedel–Crafts reaction

  摘要：

  A rapid and simple procedure for the synthesis of the indenone derivatives, N-(1-oxo-1H-inden-2-yl)benzamides, via intramolecular Friedel-Crafts (IFC) reaction of (Z)-4-arylidene-2-phenyl-5(4)-oxazolones (azlactones) catalyzed by H3PW12O40 supported on neutral alumina under microwave irradiation has been developed. The reaction is straightforward and allows easy isolation of the product. The catalyst could be re-used up to four times after simple filtration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.120
• 作为产物：
  描述：

  苯甲酰氯 在 sodium acetate 、 sodium hydroxide 作用下， 反应 3.0h， 生成 4-(3-bromobenzylidene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  四氢咪唑并[1,2-a]吡啶-5（1 H）-一衍生物的合成及杀虫性能评价

  摘要：

  摘要通过实际的氮杂反应合成了一系列新颖的含负电药效团（CNO2）的四氢咪唑并[1,2-a]吡啶-5（1H）-衍生物，并通过1H NMR，13C NMR，19F NMR和HRMS进行了表征。 。初步的生物分析表明，某些目标化合物在500 mg L-1下对褐飞虱（Nilaparvata lugens）和cow豆蚜虫（Aphis craccivora）表现出良好的杀虫活性。其中，化合物11h对100 mg L-1的褐飞虱具有活性。杀虫活性根据取代基的类型和模式而有很大不同，这为进一步研究结构修饰提供了指导。

  DOI：

  10.1016/j.cclet.2015.10.002

文献信息

• Novel and chemoselective one-pot synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones starting from benzyl alcohols promoted by [(C14H24N4)2W10O32]-[bmim]NO3
  作者：Mahboubeh Rostami、Ahmad Reza Khosropour、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad

  DOI：10.1007/s00706-011-0533-3

  日期：2011.11

  AbstractA new and practical promoter system for one-pot, efficient, chemoselective synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones using [(C14H24N4)2W10O32]-[bmim]NO3 under solvent-free conditions is described. The present work opens up a new and ecofriendly synthetic route to Erlenmeyer–Plöchl adducts from primary benzyl alcohols in a one-pot operation. Graphical abstract

  摘要一种新型实用的促进剂体系，可使用[（C 14 H 24 N 4）2 W 10 O 32 ]-[bmim进行一锅高效化学选择合成4-亚芳基-2-苯基-5（4 H）-恶唑酮描述了在无溶剂条件下的] NO 3。目前的工作为一锅操作从伯苄醇到Erlenmeyer-Plöchl加合物的合成开辟了一条新的环保途径。 图形概要
• 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。
• Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents
  作者：Xiaoke Gu、Yinpeng Zhang、Yueting Zou、Xin Li、Mingyu Guan、Qingqing Zhou、Jingying Qiu

  DOI：10.1016/j.bmc.2020.115892

  日期：2021.1

  As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value

  作为我们先前工作的延续，设计并合成了一系列新的苯基丙烯酰胺衍生物（4Aa-g，4Ba-t，5和6a-c）作为非核苷类抗HBV剂。其中，化合物4Bs可以有效抑制野生型和拉米夫定（3TC）/恩替卡韦耐药HBV突变株中HBV DNA复制，IC 50值分别为0.19和0.18μM。值得注意的是，4Bs的选择性指数值高于526，表明安全性良好。有趣的是，不像核苷类似物3TC，4BS能显著禁止3.5kb的pgRNA表达。分子对接研究表明4B通过疏水，π-π和H键相互作用可以很好地适合HBV核心蛋白的二聚体-二聚体界面。考虑到强效的抗HBV活性，低毒性以及与核苷类抗HBV药物3TC不同的抗HBV机理，化合物4Bs有望成为开发新型非核苷类抗HBV治疗药物的有希望的线索，并值得进一步研究。
• Construction of adjacent spiro-quaternary and tertiary stereocenters through phosphine-catalyzed asymmetric [3+2] annulation of allenoates with alkylidene azlactones
  作者：De Wang、Yin Wei、Min Shi

  DOI：10.1039/c2cc17709a

  日期：——

  A novel axially chiral spiro-phosphine-catalyzed highly regio-, diastereo- and enantioselective [3+2] cycloaddition of alkylidene azlactones with various allenic esters has been developed, affording the corresponding functionalized spirocyclic products in moderate to excellent yields under mild conditions. These spirocyclic products as masked amino acids can be easily transformed into aspartic amino

  已开发出一种新型的轴向手性螺膦催化的亚烷基氮杂内酯与各种烯丙基酯的高度区域，非对映和对映选择性[3 + 2]环加成反应，可在温和条件下以中等至优异的收率提供相应的官能化螺环产物。这些螺环产物作为被掩盖的氨基酸可以容易地转化为天冬氨酸类似物。
• [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。