(4E)-4-(4-nitrobenzylidene)-2-phenyloxazol-5(4H)-one | 57427-96-0

• 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: (4E)-4-(4-nitrobenzylidene)-2-phenyloxazol-5(4H)-one
• 英文别名: (4E)-4-(4-Nitrobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one；(4E)-4-[(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 57427-96-0
• 化学式: C₁₆H₁₀N₂O₄
• 分子量: 294.266
• InChiKey: QRDLKEDMXPGLTP-GXDHUFHOSA-N

物化性质

• 熔点：
  113 °C(Solv: ethanol (64-17-5); hexane (110-54-3); water (7732-18-5))
• 沸点：
  436.8±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 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：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4E)-4-(4-nitrobenzylidene)-2-phenyloxazol-5(4H)-one 在 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-[7-(4-nitrophenyl)-5-oxo-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidin-6-yl]benzamide
  参考文献：
  名称：

  2-芳基-4-亚芳基-4H-恶唑-5-酮与3-氨基-1,2,4-三唑、5-氨基四唑和2-氨基苯并咪唑的反应

  摘要：

  研究了 3-氨基-1,2,4-三唑、5-氨基四唑和 2-氨基苯并咪唑与 2-芳基-4-亚芳基-4H-恶唑-5-酮（azlactones）的反应。唑环的电子释放特性被证明会影响吖内酯与氨基唑的反应途径。所得化合物的结构通过 1H 和 13C NMR 光谱使用自旋-自旋去耦和核 Overhauser 效应确定。

  DOI：

  10.1007/s11172-005-0200-0
• 作为产物：
  描述：

  (Z)-2-phenyl-4-(4-nitrobenzylidene)-(4H)-1,3-oxazol-5-one 以 乙腈 为溶剂， 以20%的产率得到(4E)-4-(4-nitrobenzylidene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  Benzylidene–oxazolones as photoswitches: photochemistry and theoretical calculations

  摘要：

  The photophysics and photochemistry of a family of compounds proposed as efficient molecular photoswitches is presented. The effect of different light sources, substituents and solvents in the photostationary state has been explored. A detailed mechanistic description is also discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.009

文献信息

• Silica-supported Solvent Approaches More Facile than the Conventional for Erlenmeyer Synthesis with Our Pyridinium Salts
  作者：Chitrarasu Manikandan、Kilivelu Ganesan

  DOI：10.1002/jhet.3120

  日期：2018.4

  The synthesis of pyridinium salts by both conventional/silica‐supported muffle furnace and microwave approaches is described. We have optimized the Erlenmeyer synthesis of azalactone with various concentrations of our synthesized pyridinium salts. Among these, bromide‐containing pyridinium salts showed excellent catalytic activity than the others.

  描述了通过常规/二氧化硅支撑的马弗炉和微波方法合成吡啶鎓盐的方法。我们用各种浓度的合成吡啶鎓盐优化了氮杂内酯的Erlenmeyer合成。其中，含溴的吡啶鎓盐显示出优异的催化活性。
• An expedient synthesis of oxazolones using a cellulose supported ionic liquid phase catalyst
  作者：Rajanikant Kurane、Sharanabasappa Khanapure、Dolly Kale、Rajashri Salunkhe、Gajanan Rashinkar

  DOI：10.1039/c6ra03873e

  日期：——

  A novel cellulose supported ionic liquid phase catalyst containing hydroxide ions ([CellFemImi]OH) has been synthesized by covalent anchoring of 1-N-ferrocenylmethyl imidazole in the functionalized cellulose matrix followed by an anion metathesis reaction. The [CellFemImi]OH was characterized by various techniques including FT-IR, FT-Raman, 13C solid state NMR, X-ray diffraction, energy dispersive

  通过将1- N-二茂铁基甲基咪唑共价锚定在官能化纤维素基质中，然后进行阴离子复分解反应，已经合成了一种新型的含氢氧根离子的纤维素负载型离子液体催化剂。[CellFemImi] OH通过多种技术进行表征，包括FT-IR，FT-Raman，13 C固态NMR，X射线衍射，能量色散X射线（EDX）分析，场发射扫描电子显微镜（FESEM）和热重分析分析。通过在乙酸酐存在下芳基醛与马尿酸的环缩合反应，[CellFemImi] OH可有效地用作异唑类合成恶唑酮的催化剂。
• Practical Synthesis of 4-Benzylidene-2-phenyl-5(4<i>H</i>)-oxazolones
  作者：V. Siddaiah、G. Mahaboob Basha、D. Sudhakar、R. Srinuvasarao、Y. Santosh Kumar

  DOI：10.1080/00397911.2012.696301

  日期：2013.8.18

  Abstract A simple and alternative method has been developed for the synthesis of 4-benzylidene-2-phenyl-5(4H)-oxazolones via reactions of hippuric acid with various aldehydes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine/N-methylmorpholine at 75 °C. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental

  摘要 在 2-氯-4,6-二甲氧基-1 存在下，马尿酸与各种醛反应合成 4-苯亚甲基-2-苯基-5(4H)-恶唑酮，已开发出一种简单的替代方法。 ,3,5-三嗪/N-甲基吗啉在 75 °C。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Oxazolone analogs as amyloid aggregation inhibitors and for the treatment of alzheimer's disease and disorders related to amyloidosis
  申请人：——

  公开号：US20040180943A1

  公开（公告）日：2004-09-16

  Disclosed are compounds of the Formula I 1 and their use in a method of inhibiting the aggregation of amyloid proteins and in a method of imaging amyloid deposits.

  揭示了Formula I1的化合物及其在抑制淀粉样蛋白聚集的方法和成像淀粉样沉积的方法中的应用。
• Oxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships
  作者：Khalid Mohammed Khan、Uzma Rasool Mughal、Mahmud Tareq Hassan Khan、Zia-Ullah、Shahnaz Perveen、Muhammad Iqbal Choudhary

  DOI：10.1016/j.bmc.2006.05.014

  日期：2006.9

  The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosinase inhibitory properties having IC50 values in the range of 1.23 +/- 0.37-17.73 +/- 2.69 mu M, whereas standard inhibitors L-mimosine and kojic acid have IC50 values 3.68 +/- 0.02 and 16.67 +/- 0.52 mu M,, respectively. Compounds 4-8 having IC50 values 3.11 +/- 0.95, 3.51 +/- 0.25, 3.23 +/- 0.66, 1.23 +/- 0.37, and 2.15 +/- 0.75, respectively, were found to be very active members of the series, even better than both the standard inhibitors. However, compounds 3, 9-11, 13, 14, 16, 17, and 19 were found to be better than kojic acid but not L-mimosine. (2-Methyl-4-[E,2Z)-3-phenyl-2-propenyliden]-1,3-oxazol-5(4H)-one (7) bearing a cinnamyol residue at C-4 of oxazolone moiety and an IC50 = 1.23 +/- 0.37 mu M was found to be the most active one among all tested compounds. These studies reveal that the substitution of functional group (s) at C-4 and C-2 positions plays a vital role in the activity of this series of compounds. It is concluded that compound 7 may act as a potential lead molecule to develop new drugs for the treatment of tyrosinase based disorders. (c) 2006 Elsevier Ltd. All rights reserved.