3-benzoyl-4-benzylamino-7-(dimethylamino)coumarin | 1429808-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-4-benzylamino-7-(dimethylamino)coumarin
• 英文别名: 3-Benzoyl-4-(benzylamino)-7-(dimethylamino)chromen-2-one
• CAS: 1429808-64-9
• 化学式: C₂₅H₂₂N₂O₃
• 分子量: 398.461
• InChiKey: XEWYNXHKFILULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzoyl-4-benzylamino-7-(dimethylamino)coumarin 在 氧气 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以80%的产率得到N-[3-benzoyl-4-(benzylamino)-2-oxochromen-7-yl]-N-methylformamide
  参考文献：
  名称：

  Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7-dimethylaminocoumarin

  摘要：

  3-Benzoyl-4-benzylamino-7-dimethylaminocoumarin was synthesized and its conformation in solid state and solution was determined. While the X-ray crystal analysis showed an aromatic pi-pi stacking interaction in the solid state, the proton NMR studies suggested the presence of an intramolecular hydrogen bonding in solution. Adjacent functional group modifications through N-methylation, reduction of carbonyl group, or replacing the coumarin moiety to dimedone, all resulted in disrupting the pi-pi stacking conformation. Upon UV irradiation, the 7-methylamino group can be oxidized by molecular oxygen to the corresponding formamide in the absence of any external photosensitizers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.016
• 作为产物：
  描述：

  3-benzoyl-7-N,N-dimethylamino-4-hydroxychromen-2-one 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 3-benzoyl-4-benzylamino-7-(dimethylamino)coumarin
  参考文献：
  名称：

  Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7-dimethylaminocoumarin

  摘要：

  3-Benzoyl-4-benzylamino-7-dimethylaminocoumarin was synthesized and its conformation in solid state and solution was determined. While the X-ray crystal analysis showed an aromatic pi-pi stacking interaction in the solid state, the proton NMR studies suggested the presence of an intramolecular hydrogen bonding in solution. Adjacent functional group modifications through N-methylation, reduction of carbonyl group, or replacing the coumarin moiety to dimedone, all resulted in disrupting the pi-pi stacking conformation. Upon UV irradiation, the 7-methylamino group can be oxidized by molecular oxygen to the corresponding formamide in the absence of any external photosensitizers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.016