1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine | 103607-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine
• 英文别名: 5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1-phenyl-1,4-dihydropyrimidine；6-[(E)-2-(dimethylamino)vinyl]-4-oxo-1-phenyl-1,4-dihydropyrimidine-5-carbonitrile；6-[(E)-2-(dimethylamino)ethenyl]-4-oxo-1-phenylpyrimidine-5-carbonitrile
• CAS: 103607-65-4
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: YENDWUIHRZNEEV-CMDGGOBGSA-N

物化性质

• 熔点：
  233-236 °C
• 沸点：
  359.0±52.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  61.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine 在 氢氧化钾 、 水 作用下， 生成 3-cyano-4-phenylamino-1,2-dihydropyridin-2-one
  参考文献：
  名称：

  Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines

  摘要：

  1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4-pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.

  DOI：

  10.1023/b:rucb.0000037857.07190.75
• 作为产物：
  描述：

  2-氰基-3-二甲基氨基-2-丁酰胺 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine
  参考文献：
  名称：

  Search for β-adrenoblockers in the 2-(2'-hydroxy-3'-isopropylaminopropoxy]-3-cyano-4-aminopyridine series

  摘要：

  DOI：

  10.1007/bf00767827

文献信息

• ——
  作者：A. S. Ivanov、N. Z. Tugusheva、N. P. Solov"eva、V. G. Granik

  DOI：10.1023/a:1021636632164

  日期：——

  The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable sigma-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting sigma-complexes are rearranged into sulfides 14a-c. Sulfides 14b,c undergo the Thorpe-Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of sigma-adducts of the C-N and C-C types, while those with aliphatic amines yield 3-amino derivatives 17a-c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.
• Pyronaridine Protects against SARS-CoV-2 Infection in Mouse
  作者：Ana C. Puhl、Giovanni F. Gomes、Samara Damasceno、Andre S. Godoy、Gabriela D. Noske、Aline M. Nakamura、Victor O. Gawriljuk、Rafaela S. Fernandes、Natalia Monakhova、Olga Riabova、Thomas R. Lane、Vadim Makarov、Flavio P. Veras、Sabrina S. Batah、Alexandre T. Fabro、Glaucius Oliva、Fernando Q. Cunha、José C. Alves-Filho、Thiago M. Cunha、Sean Ekins

  DOI：10.1021/acsinfecdis.2c00091

  日期：2022.6.10
• AZIMOV, V. A.;GRANIK, V. G.;GRIZIK, S. I.;ERSHOV, L. V.;SMETSKAYA, N. I.;+, XIM.-FARMATS. ZH., 1985, 19, N 8, 947-952
  作者：AZIMOV, V. A.、GRANIK, V. G.、GRIZIK, S. I.、ERSHOV, L. V.、SMETSKAYA, N. I.、+

  DOI：——

  日期：——
• YALYSHEVA N. Z.; SOLOVEVA N. P.; CHISTYAKOV V. V.; SHEJNKER YU. N.; GRANI+, XIMIYA GETEROTSIKL. SOED.,(1986) N 8, 1118-1123
  作者：YALYSHEVA N. Z.、 SOLOVEVA N. P.、 CHISTYAKOV V. V.、 SHEJNKER YU. N.、 GRANI+

  DOI：——

  日期：——