1-benzyl-6-methyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one | 1224738-42-4

• 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: 1-benzyl-6-methyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one
• 英文别名: N-benzyl-3,4-dihydro-6-methyl-4-phenylquinolin-2(1H)-one；1-Benzyl-6-methyl-4-phenyl-3,4-dihydroquinolin-2-one；1-benzyl-6-methyl-4-phenyl-3,4-dihydroquinolin-2-one
• CAS: 1224738-42-4
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: REKPKCXRUUAZMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯硼酸酐 、 (E)-methyl 3-(2-(benzylamino)-5-methylphenyl)acrylate 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82%的产率得到1-benzyl-6-methyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one
  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

• Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of Oxamic Acids with Alkenes towards Quinolin-2-ones
  作者：Gaofeng Feng、Chengan Jin、Jing-Yao He、Qi-Fan Bai

  DOI：10.1055/s-0040-1707891

  日期：2020.9

  An efficient silver-catalyzed tandem decarboxylative radical addition/cyclization of oxamic acids with alkenes has been developed. This method provides a novel and straightforward protocol toward a variety of 4-aryl-3,4-dihydroquinolin-2(1H)-ones, 4-(α-carbonyl)-3,4-dihydroquinolin-2(1H)-ones, and quinolin-2(1H)-ones in aqueous solution.

  已开发出一种有效的银催化串联脱羧自由基加成/环化草酸与烯烃。该方法为各种 4-芳基-3,4-二氢喹啉-2(1H)-酮、4-(α-羰基)-3,4-二氢喹啉-2(1H)-酮、和 quinolin-2(1H)-ones 在水溶液中。
• Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of <i>N</i>- and <i>O</i>-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles
  作者：Ja Ock Park、So Won Youn

  DOI：10.1021/ol100610v

  日期：2010.5.21

  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.