(5S,7S,8R)-5,6,7,8-tetrahydro-6,6-dimethyl-8-phenylmethyl-2-quinolinyl-5,7-methanoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (5S,7S,8R)-5,6,7,8-tetrahydro-6,6-dimethyl-8-phenylmethyl-2-quinolinyl-5,7-methanoquinoline
• 英文别名: (1S,8R,9S)-8-benzyl-10,10-dimethyl-5-quinolin-2-yl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
• 化学式: C₂₈H₂₆N₂
• 分子量: 390.528
• InChiKey: KSSAECQFXHARLL-ZLNRFVROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄基碘 、 (5S,7S)-5,6,7,8-tetrahydro-6,6-dimethyl-2-quinolinyl-5,7-methanoquinoline 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以35%的产率得到(5S,7S,8R)-5,6,7,8-tetrahydro-6,6-dimethyl-8-phenylmethyl-2-quinolinyl-5,7-methanoquinoline
  参考文献：
  名称：

  Chiral 2,2′-bipyridines, 5,6-dihydro-1,10-phenanthrolines and 1,10-phenanthrolines as ligands for enantioselective palladium catalyzed allylic substitution

  摘要：

  A number of chiral 5,6-dihydro-1,1-phenanthrolines, 5,6-dihydrobenzo[b]-1,1-phenanthrolines and 5,6,7,8-tetrahydro-2-quinolinylquinoline derived from (-)-pinocarvone were prepared and assessed in the enantioselective palladium catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl-malonate. The introduction of a benzo-fused substituent on the pyridine ring not containing the chiral backbone resulted in the drastic reduction of the stereoselectivity of the reaction. Enantioselectivities up to 81% were obtained. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00296-2

文献信息

• Chiral 2,2′-bipyridines, 5,6-dihydro-1,10-phenanthrolines and 1,10-phenanthrolines as ligands for enantioselective palladium catalyzed allylic substitution
  作者：Giorgio Chelucci、Antonio Saba、Gianuario Sanna、Franco Soccolini

  DOI：10.1016/s0957-4166(00)00296-2

  日期：2000.8

  A number of chiral 5,6-dihydro-1,1-phenanthrolines, 5,6-dihydrobenzo[b]-1,1-phenanthrolines and 5,6,7,8-tetrahydro-2-quinolinylquinoline derived from (-)-pinocarvone were prepared and assessed in the enantioselective palladium catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl-malonate. The introduction of a benzo-fused substituent on the pyridine ring not containing the chiral backbone resulted in the drastic reduction of the stereoselectivity of the reaction. Enantioselectivities up to 81% were obtained. (C) 2000 Published by Elsevier Science Ltd.