4-(o-nitrobenzylidene)-2-methyl-5-oxazolone

• 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-(o-nitrobenzylidene)-2-methyl-5-oxazolone
• 英文别名: (Z)-2-Methyl-4-(2-nitrobenzylidene)oxazol-5(4H)-one；2-methyl-4-[(2-nitrophenyl)methylidene]-1,3-oxazol-5-one
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: KBBINJZIGXCCNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  4-(o-nitrobenzylidene)-2-methyl-5-oxazolone 在 盐酸 、 溶剂黄146 作用下， 反应 6.0h， 以0.76 g的产率得到邻硝基苯基丙酮酸
  参考文献：
  名称：

  苯基丙酮酸中的酮/烯醇互变异构：邻硝基苯基丙酮酸的结构

  摘要：

  摘要 在邻硝基苯甲醛的吖内酯酸水解后合成了邻硝基苯丙酮酸的互变异构酮/烯醇混合物。两种互变异构形式的结构通过 NMR 光谱确定。单晶的 X 射线衍射表明晶型对应于酮互变异构体。气相中的量子力学计算证实了溶液中的实验结果。

  DOI：

  10.1016/s0022-2860(99)00323-3
• 作为产物：
  描述：

  邻硝基苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 生成 4-(o-nitrobenzylidene)-2-methyl-5-oxazolone
  参考文献：
  名称：

  Synthesis, Photophysical Properties, and Application of o- and p-Amino Green Fluorescence Protein Synthetic Chromophores

  摘要：

  The o- and p-amino green-fluorescence-protein synthetic chromophores (GFPSCs) were synthesized from the corresponding o- and p-nitro protecting group. Among the four protecting groups of the o-amino group, the o-nitro protecting group is the only choice to synthesize the o-amino GFPSCs. The first singlet excited states of o- and p-amino GFPSCs carry significant charge-transfer character through the mechanism of photoinduced charge transfer (PCT). The o-amino GFPSCs can serve as wavelength-ratiometric fluorescence sensors that selectively recognize Cr3+ in aqueous medium through a PCT mechanism.

  DOI：

  10.1021/jo302050y

文献信息

• Keto/enol tautomerism in phenylpyruvic acids: structure of the o-nitrophenylpyruvic acid
  作者：A.J.M. Carpy、P.P. Haasbroek、J. Ouhabi、D.W. Oliver

  DOI：10.1016/s0022-2860(99)00323-3

  日期：2000.3

  synthesis of a tautomeric keto/enol mixture of o-nitrophenylpyruvic acid followed the acid hydrolysis of the azlactone of o-nitrobenzaldehyde was carried out. The structures of the two tautomeric forms were assigned by NMR spectroscopy. X-ray diffraction of a single crystal revealed that the crystalline form corresponds to the keto tautomer. Quantum mechanics calculations in the gas phase confirmed the

  摘要 在邻硝基苯甲醛的吖内酯酸水解后合成了邻硝基苯丙酮酸的互变异构酮/烯醇混合物。两种互变异构形式的结构通过 NMR 光谱确定。单晶的 X 射线衍射表明晶型对应于酮互变异构体。气相中的量子力学计算证实了溶液中的实验结果。
• Microwave-assisted synthesis and antimicrobial screening of new imidazole derivatives bearing 4-thiazolidinone nucleus
  作者：N. C. Desai、V. V. Joshi、K. M. Rajpara、H. V. Vaghani、H. M. Satodiya

  DOI：10.1007/s00044-012-0190-z

  日期：2013.4

  A new series of compounds 2-((1-(4-(4-arylidene-2-methyl-5-oxo-4,5-dihydro-1H-imidazol-1-yl)phenyl)ethylidene)hydrazono)thiazolidin-4-ones (4a-o) have been synthesized under conventional and microwave irradiation method. All compounds were characterized by IR, H-1 NMR, C-13 NMR and mass spectra. Newly synthesized compounds were screened for their antibacterial and antifungal activities on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogenes, Candida albicans, Aspergillus niger and Aspergillus clavatus by bioassays, namely serial broth dilution. The synthesized compounds showed potent antimicrobial activity against tested microorganisms. Compounds 4h, 4j, 4m and 4n were the most potent amongst tested compounds.
• Siddiqui, Ibadur R.; Singh, Pravin K.; Srivastava, Vishal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 4, p. 512 - 520
  作者：Siddiqui, Ibadur R.、Singh, Pravin K.、Srivastava, Vishal、Singh

  DOI：——

  日期：——
• PHENYLPYRUVIC ACID DERIVATIVES AS ENZYME INHIBITORS: THERAPEUTIC POTENTIAL ON MACROPHAGE MIGRATION INHIBITORY FACTOR
  作者：Alain J.M. Carpy、Petrus P. Haasbroeck、Douglas W. Oliver

  DOI：10.1007/s00044-004-0102-y

  日期：2004.10

  Phenylpyruvic acid derivatives are obtained by hydrolysing aromatic Z/E azlactones. Keto tautomers interact with enzyme systems such as phenylalanine dehydrogenase or carboxypeptidase A whereas enol tautomers are potential inhibitors on the phenylpyruvate tautomerase activity catalysed by Macrophage Migration Inhibitory Factor (MIF). MIF being a key molecule in immune and inflammatory processes several structures with reasonable interaction with MIF and protocol for specific synthesis are presented.
• Synthesis, Photophysical Properties, and Application of <i>o</i>- and <i>p</i>-Amino Green Fluorescence Protein Synthetic Chromophores
  作者：Yi-Hui Chen、Wei-Jen Lo、Kuangsen Sung

  DOI：10.1021/jo302050y

  日期：2013.1.18

  The o- and p-amino green-fluorescence-protein synthetic chromophores (GFPSCs) were synthesized from the corresponding o- and p-nitro protecting group. Among the four protecting groups of the o-amino group, the o-nitro protecting group is the only choice to synthesize the o-amino GFPSCs. The first singlet excited states of o- and p-amino GFPSCs carry significant charge-transfer character through the mechanism of photoinduced charge transfer (PCT). The o-amino GFPSCs can serve as wavelength-ratiometric fluorescence sensors that selectively recognize Cr3+ in aqueous medium through a PCT mechanism.