4-Benzylamino-3-benzyl-2(1H)-chinolon | 110229-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-Benzylamino-3-benzyl-2(1H)-chinolon
• 英文别名: 3-benzyl-4-(benzylamino)-1H-quinolin-2-one
• CAS: 110229-57-7
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: CWSQZLMOLBQCKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Benzylamino-3-benzyl-2(1H)-chinolon 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以80%的产率得到4-amino-3-benzyl-2(1H)-quinolone
  参考文献：
  名称：

  Regioselective Azidation of 2,4-Dichloroquinolines

  摘要：

  Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazolo[1,5-a]quinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chloro-tetrazolo[1,5-a]quinolines (5g-i). When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo[1,5-a]quinolines (5a-i) are obtained. Structural assignments of 3 and 5 have been carried out by C-13-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9). It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.

  DOI：

  10.1002/prac.19943360407
• 作为产物：
  描述：

  3-benzyl-4-hydroxy-2-quinolone 、 苄胺 反应 12.0h， 以62%的产率得到4-Benzylamino-3-benzyl-2(1H)-chinolon
  参考文献：
  名称：

  Methoden zur Darstellung von 4-Azido-2(1H)-chinolonen

  摘要：

  DOI：

  10.1007/bf00810876

文献信息

• STADLBAUER W., MONATSH. CHEM., 117,(1986) N 11, 1305-1323
  作者：STADLBAUER W.

  DOI：——

  日期：——
• Methoden zur Darstellung von 4-Azido-2(1H)-chinolonen
  作者：Wolfgang Stadlbauer

  DOI：10.1007/bf00810876

  日期：1986.11
• Regioselective Azidation of 2,4-Dichloroquinolines
  作者：Waltraud Steinschifter、Wolfgang Stadlbauer

  DOI：10.1002/prac.19943360407

  日期：——

  Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazolo[1,5-a]quinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chloro-tetrazolo[1,5-a]quinolines (5g-i). When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo[1,5-a]quinolines (5a-i) are obtained. Structural assignments of 3 and 5 have been carried out by C-13-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9). It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.