(8S,10S)-8,10-methano-9,9-dimethyl-5,6,8,9,10,11-hexahydrobenzo[b][1,10]phenanthroline | 213979-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: (8S,10S)-8,10-methano-9,9-dimethyl-5,6,8,9,10,11-hexahydrobenzo[b][1,10]phenanthroline
• 英文别名: (1S,17S)-18,18-dimethyl-11,14-diazapentacyclo[15.1.1.02,15.04,13.07,12]nonadeca-2(15),3,7(12),8,10,13-hexaene
• CAS: 213979-83-0
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: BHCOCMKQVXWKSV-DZGCQCFKSA-N

物化性质

• 沸点：
  443.417±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.169±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8S,10S)-8,10-methano-9,9-dimethyl-5,6,8,9,10,11-hexahydrobenzo[b][1,10]phenanthroline 在 palladium on activated charcoal 萘烷 、 lithium diisopropyl amide 作用下， 反应 5.0h， 生成 (1S,16R,17S)-18,18-dimethyl-16-(2-methylpropyl)-11,14-diazapentacyclo[15.1.1.02,15.04,13.07,12]nonadeca-2(15),3,5,7(12),8,10,13-heptaene
  参考文献：
  名称：

  New 1,10-phenanthroline ligands for asymmetric catalysis: enantioselective palladium catalyzed allylic substitution

  摘要：

  A number of new chiral C-1-symmetric 1,10-phenathrolines have been prepared and assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivities up to 84% were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00279-1
• 作为产物：
  描述：

  在 ammonium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (8S,10S)-8,10-methano-9,9-dimethyl-5,6,8,9,10,11-hexahydrobenzo[b][1,10]phenanthroline
  参考文献：
  名称：

  New 1,10-phenanthroline ligands for asymmetric catalysis: enantioselective palladium catalyzed allylic substitution

  摘要：

  A number of new chiral C-1-symmetric 1,10-phenathrolines have been prepared and assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivities up to 84% were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00279-1

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.
• New 1,10-phenanthroline ligands for asymmetric catalysis: enantioselective palladium catalyzed allylic substitution
  作者：Giorgio Chelucci、Antonio Saba

  DOI：10.1016/s0957-4166(98)00279-1

  日期：1998.8

  A number of new chiral C-1-symmetric 1,10-phenathrolines have been prepared and assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivities up to 84% were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.