4-(4-Cyanbenzyliden)-2-phenyloxazolin-5-on | 51529-72-7

• 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-(4-Cyanbenzyliden)-2-phenyloxazolin-5-on
• 英文别名: 2-Phenyl-4-(4-cyanobenzylidene)oxazol-5-one；p-cyanobenzylidene-5-phenyl-1-oxazolone；2-Phenyl-4-(4-cyanbenzyliden)-oxazolinon-5；CCT129960；4-(5-oxo-2-phenyl-oxazol-4-ylidenemethyl)-benzonitrile；Benzonitrile, 4-[(5-oxo-2-phenyl-4(5H)-oxazolylidene)methyl]-；4-[(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]benzonitrile
• CAS: 51529-72-7
• 化学式: C₁₇H₁₀N₂O₂
• 分子量: 274.279
• InChiKey: TVAGPAAYXQKMPE-UHFFFAOYSA-N

物化性质

• 熔点：
  285-287 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  461.4±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 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：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-Cyanbenzyliden)-2-phenyloxazolin-5-on 在 盐酸 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 0.33h， 生成 4-((Z)-2-Benzoylamino-3-oxo-3-piperidin-1-yl-propenyl)-benzimidic acid methyl ester; hydrochloride
  参考文献：
  名称：

  Voigt, B.; Wagner, G.; Walsmann, P., Pharmazie, 1983, vol. 38, # 12, p. 835 - 838

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 在 sodium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 生成 4-(4-Cyanbenzyliden)-2-phenyloxazolin-5-on
  参考文献：
  名称：

  Chemoselective Transfer Hydrogenation of Enamides Using Ru Pincer Complexes for the Synthesis of α-Amino Acids

  摘要：

  DOI：

  10.1021/acs.joc.1c02975

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
• 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。
• Synthesis and spectroscopic analysis of benzylidene imidazolone linked to P-porphyrins through axial ligand
  作者：Jin Matsumoto、Kyosuke Takemori、Jun Ishikawa、Yu Nabetani、Mamoru Fujitsuka、Tetsuro Majima、Masahide Yasuda

  DOI：10.1007/s00044-018-2255-0

  日期：2018.12

  Tetraphenylporphyrinatophosphorus(V) complexes (1) comprising two axially linked benzylidene imidazolone (Biz) moieties, which are chromophores of the green fluorescent protein, were prepared. In medical applications such as photodynamic therapy, the P-porphyrin part (Ptp) is expected to sensitize to generate singlet oxygen, whereas the Biz units act as fluorescent probes. The fluorescence spectra

  制备了包含两个轴向连接的亚苄基咪唑酮（Biz）部分的四苯基卟啉对磷（V）络合物（1），其为绿色荧光蛋白的发色团。在诸如光动力疗法的医学应用中，预计P-卟啉部分（Ptp）会敏化产生单线态氧，而Biz单位则充当荧光探针。在370 nm的Biz激发下分析1的荧光光谱。分别在460和610 nm处观察到由Biz和Ptp激发态引起的荧光。发生了由Ptp激发的单重态Biz的分子内猝灭，导致Biz发出的荧光弱。在Biz单位1中引入氰基提高了他们的荧光量子产率高达7.7×10 -4。在550 nm的Ptp激发下1的荧光光谱与不含Biz发色团的二甲氧基四苯基卟啉氯化磷的对-卟啉参考化合物的荧光光谱极为相似。在对卟啉的轴向位置引入Biz后，Ptp的理化参数保持不变。
• CsF-Catalyzed Transannulation Reaction of Oxazolones: Diastereoselective Synthesis of Diversified <i>trans</i>-<i>N</i>-(6-Oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with Arylidene Azlactones and Amidines
  作者：Golnaz Parhizkar、Ahmad Reza Khosropour、Iraj Mohammadpoor-Baltork、Elahehnaz Parhizkar、Hadi Amiri Rudbari

  DOI：10.1021/acscombsci.8b00027

  日期：2018.6.11

  straightforward synthetic strategy for the construction of new tetrasubstituted 1,3-diazinones is described. The procedure is based on CsF-catalyzed, microwave-assisted, ring transformation reaction of arylidene azlactones with amidines. Moreover, this technique provides diversified trans-N-(6-oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with a good antimicrobial activity.

  描述了一种用于构建新的四取代的1，3-二氮杂二酮的通用且直接的合成策略。该程序基于CsF催化的亚芳基a内酯与am的微波辅助环转化反应。此外，该技术提供了多元化反式- ñ - （6-氧代-1,4,5,6-四氢嘧啶-5-基）具有良好的抗微生物活性的苯甲酰胺。