N-苄基-4-苯基-1,2,3,4-四氢喹啉-2-酮 | 697759-12-9

• 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
• 中文名称: N-苄基-4-苯基-1,2,3,4-四氢喹啉-2-酮
• 英文名称: N-benzyl-4-phenyl-1,2,3,4-tetrahydroquinolin-2-one
• 英文别名: N-benzyl-3,4-dihydro-4-phenylquinolin-2(1H)-one；1-Benzyl-4-phenyl-3,4-dihydroquinolin-2-one
• CAS: 697759-12-9
• 化学式: C₂₂H₁₉NO
• 分子量: 313.399
• InChiKey: DMFOGXCUJUIVSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  524.1±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-苄基-4-苯基-1,2,3,4-四氢喹啉-2-酮 在 三氟乙酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 以83%的产率得到3,4-二氢-4-苯基-2(1H)-喹啉
  参考文献：
  名称：

  Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

  摘要：

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

  DOI：

  10.1021/ol100610v
• 作为产物：
  描述：

  methyl 3-(2-(benzylamino)phenyl)-3-phenylpropanoate 在 hydroxo(1,5-cyclooctadiene)rhodium (I) dimer 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以40%的产率得到N-苄基-4-苯基-1,2,3,4-四氢喹啉-2-酮
  参考文献：
  名称：

  Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

  摘要：

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

  DOI：

  10.1021/ol100610v

文献信息

• The triflic acid-mediated cyclisation of N-benzylcinnamanilides
  作者：Frank D. King、Stephen Caddick

  DOI：10.1016/j.tet.2013.07.075

  日期：2013.10

  N-Benzylcinnamanilides cyclise with triflic acid to form 1-benzyl-4-aryl-2,4-dihydro-1H-quinolin-2-ones and 2,5-diaryl-benzazepin-3-ones. The product ratio is determined by the preferred orientation of the amide and by the electronics of the substituents. With ortho-substituted anilides, N-debenzylation also occurs to give 4-aryl-2,4-dihydro-1H-quinoline-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.
• The triflic acid-mediated cyclisation of N-benzyl-cinnamamides
  作者：Frank D. King、Stephen Caddick

  DOI：10.1016/j.tet.2012.11.035

  日期：2013.1

  N-Benzyl-cinnamamides cyclise with triflic acid to form 5-aryl-benzazepinones and/or cinnamamides. (c) 2012 Elsevier Ltd. All rights reserved.