4-{4-[3-(3,4-dimethoxyphenyl)acryloyl]phenylamino}chromen-2-one | 1375461-75-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-{4-[3-(3,4-dimethoxyphenyl)acryloyl]phenylamino}chromen-2-one
• CAS: 1375461-75-8
• 化学式: C₂₆H₂₁NO₅
• 分子量: 427.456
• InChiKey: LUCAMDQWQUFWOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  77.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-{4-[3-(3,4-dimethoxyphenyl)acryloyl]phenylamino}chromen-2-one 、 溶剂黄146 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 以72%的产率得到4-{4-[1-acetyl-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenylamino}chromen-2-one
  参考文献：
  名称：

  In vitro antimicrobial and antimycobacterial activity of some chalcones and their derivatives

  摘要：

  In this study, novel series of chalcone derivatives, namely, 4-[4-(3-phenyl-acryloyl)-phenylamino]-chromen-2-one (5a-k) have been synthesized from the intermediate 4-(4-acetyl-phenylamino)-chromen-2-one (4). Cyclization reaction of chalcone (5a-k) with hydrazine hydrate, guanidine nitrate, and malononitrile gives the corresponding 4-[4-(1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-phenylamino]-chromen-2-one (6a-k), 4-[4-(2-amino-6-phenyl-pyrimidin-4-yl)-phenylamino]-chromen-2-one (7a-k), and 2-amino-6-[4-(2-oxo-2H-chromen-4-ylamino)-phenyl]-4-phenyl-nicotinonitrile (8a-k) derivatives were synthesized. The newly synthesized compounds were evaluated for their antimycobacterial activity and antimicrobial activity against eight bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneri) and four fungi (A. niger, C. albicans, A. fumigatus, and A. clavatus).

  DOI：

  10.1007/s00044-012-0073-3
• 作为产物：
  描述：

  4-羟基香豆素 在 potassium hydroxide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.0h， 生成 4-{4-[3-(3,4-dimethoxyphenyl)acryloyl]phenylamino}chromen-2-one
  参考文献：
  名称：

  In vitro antimicrobial and antimycobacterial activity of some chalcones and their derivatives

  摘要：

  In this study, novel series of chalcone derivatives, namely, 4-[4-(3-phenyl-acryloyl)-phenylamino]-chromen-2-one (5a-k) have been synthesized from the intermediate 4-(4-acetyl-phenylamino)-chromen-2-one (4). Cyclization reaction of chalcone (5a-k) with hydrazine hydrate, guanidine nitrate, and malononitrile gives the corresponding 4-[4-(1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-phenylamino]-chromen-2-one (6a-k), 4-[4-(2-amino-6-phenyl-pyrimidin-4-yl)-phenylamino]-chromen-2-one (7a-k), and 2-amino-6-[4-(2-oxo-2H-chromen-4-ylamino)-phenyl]-4-phenyl-nicotinonitrile (8a-k) derivatives were synthesized. The newly synthesized compounds were evaluated for their antimycobacterial activity and antimicrobial activity against eight bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneri) and four fungi (A. niger, C. albicans, A. fumigatus, and A. clavatus).

  DOI：

  10.1007/s00044-012-0073-3