(±)-ethyl 4-(furan-2-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate | 1022919-17-0

• 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
• 英文名称: (±)-ethyl 4-(furan-2-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: 3-carboethoxy-4-(2-furyl)-2-methyl-4,5-dihydropyridin-6-one；ethyl 4-(furan-2-yl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 1022919-17-0
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: KQWVICMSFKEFBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠醛 、 乙酰乙酸乙酯 在 Bi(NO₃)3*ZnCl₂*Al₂O₃ 乙酰胺 作用下， 以70%的产率得到(±)-ethyl 4-(furan-2-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Simple and efficient one‐pot synthesis of 3,4‐dihydro‐2‐pyridones via solid‐supported Bi(III)nitrate catalyzed double michael addition‐azaannulation

  摘要：

  Abstractmagnified image4‐Aryl‐5‐carboethoxy‐6‐methyl‐2,3‐dihydro‐2‐pyridones were obtained, in high yield, by heating ternary mixtures of appropriate aldehydes, ethylacetoacetate and compounds possessing NH2‐C=X functionality, in presence of immobilized Bi(III)nitrate and co‐catalyst Zn(II)chloride, under solventless conditions. The reaction proceeds smoothly at 140±5°C and seems to involve double Michael addition‐azaannulation.

  DOI：

  10.1002/jhet.5570450209

文献信息

• Discovery of Potent and Highly Selective A_2B Adenosine Receptor Antagonist Chemotypes
  作者：Abdelaziz El Maatougui、Jhonny Azuaje、Manuel González-Gómez、Gabriel Miguez、Abel Crespo、Carlos Carbajales、Luz Escalante、Xerardo García-Mera、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1021/acs.jmedchem.5b01586

  日期：2016.3.10

  novel families of A2B adenosine receptor antagonists were identified in the context of the structural exploration of the 3,4-dihydropyrimidin-2(1H)-one chemotype. The most appealing series contain imidazole, 1,2,4-triazole, or benzimidazole rings fused to the 2,3-positions of the parent diazinone core. The optimization process enabled identification of a highly potent (3.49 nM) A2B ligand that exhibits

  在3,4-dihydropyrimidin- 2-2 （1 H）-one化学型的结构探索的背景下，确定了三个新的A 2B腺苷受体拮抗剂家族。最具吸引力的系列包含与母体重氮酮核心的2,3-位稠合的咪唑，1,2,4-三唑或苯并咪唑环。通过优化过程，可以鉴定出对A 1，A 2A和A 3表现出完全选择性的高效（3.49 nM）A 2B配体受体。功能性cAMP实验的结果证实了代表性配体的拮抗作用。通过基于基于人A 2A受体晶体结构构建的受体驱动的对接模型的分子模型研究，证实了该系列中鉴定出的主要SAR趋势。
• Simple and efficient one‐pot synthesis of 3,4‐dihydro‐2‐pyridones via solid‐supported Bi(III)nitrate catalyzed double michael addition‐azaannulation
  作者：Jagjeet Singh、Summon Koul、Rattan L. Sharma、Tej K. Razdan、Ajay P. S. Pannu

  DOI：10.1002/jhet.5570450209

  日期：2008.3

  Abstractmagnified image4‐Aryl‐5‐carboethoxy‐6‐methyl‐2,3‐dihydro‐2‐pyridones were obtained, in high yield, by heating ternary mixtures of appropriate aldehydes, ethylacetoacetate and compounds possessing NH2‐C=X functionality, in presence of immobilized Bi(III)nitrate and co‐catalyst Zn(II)chloride, under solventless conditions. The reaction proceeds smoothly at 140±5°C and seems to involve double Michael addition‐azaannulation.