4-羟基-2-甲基-6-氧代-5-苯基-1H-吡啶-3-羧酸乙酯 | 76066-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-羟基-2-甲基-6-氧代-5-苯基-1H-吡啶-3-羧酸乙酯
• 英文名称: 5-Ethoxycarbonyl-4-hydroxy-6-methyl-3-phenyl-2-pyridon
• 英文别名: ethyl 4-hydroxy-6-methyl-3-phenyl-2-oxo-1,2-dihydropyridine-5-carboxylate；ethyl 4-hydroxy-6-methyl-2-oxo-3-phenyl-1,2-dihydropyridine-5-carboxylate；4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester；Ethyl 4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydropyridine-3-carboxylate；ethyl 4-hydroxy-2-methyl-6-oxo-5-phenyl-1H-pyridine-3-carboxylate
• CAS: 76066-86-9
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: WCTVEONIUSTFIF-UHFFFAOYSA-N

物化性质

• 熔点：
  300-302 °C(Solv: ethanol (64-17-5))
• 沸点：
  457.8±45.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基-2-甲基-6-氧代-5-苯基-1H-吡啶-3-羧酸乙酯 在 sodium hydroxide 作用下， 反应 2.0h， 以93%的产率得到4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones

  摘要：

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.

  DOI：

  10.1016/0223-5234(91)90194-r
• 作为产物：
  描述：

  3-氨基巴豆酸乙酯 、 苯基丙二酸二乙酯 反应 3.0h， 以52%的产率得到4-羟基-2-甲基-6-氧代-5-苯基-1H-吡啶-3-羧酸乙酯
  参考文献：
  名称：

  Stadlbauer, Wolfgang; Fiala, Werner; Fischer, Michaela, Advanced Synthesis and Catalysis, 2000, vol. 342, # 1, p. 33 - 39

  摘要：

  DOI：

文献信息

• Synthese von Isocumarinen aus Phenylmalonylheterocyclen /Synthesis of Isocoumarines from Phenylmalonyl Heterocyclic Compounds
  作者：Wolfgang Stadlbauer、Nadia Ghobrial、Thomas Kappe

  DOI：10.1515/znb-1980-0719

  日期：1980.7.1

  Reaction of diphenylcarbonate (2) with enolized phenylmalonyl heterocyclic compounds as the quinolones 1 a-c, the quinolizinones 4 or the phenalenones 6 a, b yields the condensed isocoumarines 3 a-c, 5 or 7 a, b, respectively. Contrary to these results 3-hydroxy-2-phenyl-chinchonic acid (8) or its decarboxylated product 10 do not form the expected isocoumarin 9 but afford the diquinolino-γ-pyrone 11

  二苯碳酸酯（2）与烯醇化苯马来酰杂环化合物如喹诺酮1a-c、喹诺酮4或苯并酮6a、b反应，分别得到缩合异咖啡因3a-c、5或7a、b。与这些结果相反，3-羟基-2-苯基-奎奴酸（8）或其脱羧产物10不形成预期的异咖啡因9，而是产生二喹啉基-γ-吡喃酮11。
• 4-Hydroxyquinolones-2. 91. Synthesis and properties of ethyl 1-R-4-hydroxy-6-methyl-2-oxo-dihydropyridine-5-carboxylates
  作者：I. V. Ukrainets、L. V. Sidorenko、O. V. Gorokhova、O. V. Shishkin

  DOI：10.1007/s10593-006-0070-x

  日期：2006.2
• STADLBAUER W.; GHOBRIAL N.; KAPPE T., Z. NATURFORSCH., 1980, B 35, NO 7, 892-895
  作者：STADLBAUER W.、 GHOBRIAL N.、 KAPPE T.

  DOI：——

  日期：——
• Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones
  作者：G Dannhardt、W Meindl、BD Schober、T Kappe

  DOI：10.1016/0223-5234(91)90194-r

  日期：1991.9

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.
• Stadlbauer, Wolfgang; Fiala, Werner; Fischer, Michaela, Advanced Synthesis and Catalysis, 2000, vol. 342, # 1, p. 33 - 39
  作者：Stadlbauer, Wolfgang、Fiala, Werner、Fischer, Michaela、Hojas, Gerhard

  DOI：——

  日期：——