4,4'-bis((8S,9S)-6'-methoxycinchonan-9-yl)biphenyl | 1052635-08-1

• 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: 4,4'-bis((8S,9S)-6'-methoxycinchonan-9-yl)biphenyl
• 英文别名: 4-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-[4-[4-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]phenyl]phenyl]methyl]-6-methoxyquinoline
• CAS: 1052635-08-1
• 化学式: C₅₂H₅₄N₄O₂
• 分子量: 767.026
• InChiKey: IEQGOMBNCILZLG-AOYYWVCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  58
• 可旋转键数：
  11
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-bis((8S,9S)-6'-methoxycinchonan-9-yl)biphenyl 在 10% Pd on charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到4,4'-bis((8S,9S)-10,11-dihydro-6'-methoxycinchonan-9-yl)biphenyl
  参考文献：
  名称：

  Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New C₂-Symmetric Dimers

  摘要：

  An unexpected stereoselective direct dimerization Occurred when 9-quinine halide was treated with butyllithium. The reaction of either (9S)- or (9R)-chloroquinine gave the same C-2-symmetric dimer with 9R configuration (X-ray structure). A tentative mechanism involving radical recombination is discussed. This highly congested dimer forms two atropisomers, and their reversible interconversion was studied by NMR. Another C-2-symmetric (9S)-quinine dinner connected solely by carbon-carbon bonds was obtained by the stereoselective coupling of bis(arylbromomagnesium) derivative with (9S)-chloroquinine.

  DOI：

  10.1021/jo801205n
• 作为产物：
  描述：

  4,4'-二溴联苯 、 9-desoxy-9-chloroquinine 在 氢化钾 、 magnesium chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.5h， 以30%的产率得到4,4'-bis((8S,9S)-6'-methoxycinchonan-9-yl)biphenyl
  参考文献：
  名称：

  Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New C₂-Symmetric Dimers

  摘要：

  An unexpected stereoselective direct dimerization Occurred when 9-quinine halide was treated with butyllithium. The reaction of either (9S)- or (9R)-chloroquinine gave the same C-2-symmetric dimer with 9R configuration (X-ray structure). A tentative mechanism involving radical recombination is discussed. This highly congested dimer forms two atropisomers, and their reversible interconversion was studied by NMR. Another C-2-symmetric (9S)-quinine dinner connected solely by carbon-carbon bonds was obtained by the stereoselective coupling of bis(arylbromomagnesium) derivative with (9S)-chloroquinine.

  DOI：

  10.1021/jo801205n