tert-butyl (S)-3-(4-fluorobenzyl)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate | 1620102-59-1

• 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: tert-butyl (S)-3-(4-fluorobenzyl)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate
• 英文别名: tert-butyl (3S)-3-[(4-fluorophenyl)methyl]-2-oxo-3,4-dihydroquinoline-1-carboxylate
• CAS: 1620102-59-1
• 化学式: C₂₁H₂₂FNO₃
• 分子量: 355.409
• InChiKey: LWLWRWPJHFMSOW-INIZCTEOSA-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-氟苯基)丙酸 、 tert-butyl (2-(chloromethyl)phenyl)carbamate 在 咪唑 、 (R)-5-benzyl-2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 caesium carbonate 、 N,N'-羰基二咪唑 作用下， 反应 15.0h， 以84%的产率得到
  参考文献：
  名称：

  Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates

  摘要：

  A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

  DOI：

  10.1021/ja505880r

文献信息

• Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates
  作者：Anna Lee、Ashkaan Younai、Christopher K. Price、Javier Izquierdo、Rama K. Mishra、Karl A. Scheidt

  DOI：10.1021/ja505880r

  日期：2014.7.30

  A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.