bis((8S,9R)-6'-methoxycinchonan-9-yl) | 1052635-10-5

• 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: bis((8S,9R)-6'-methoxycinchonan-9-yl)
• 英文别名: 4-[(1R,2R)-1,2-bis[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-2-(6-methoxyquinolin-4-yl)ethyl]-6-methoxyquinoline
• CAS: 1052635-10-5
• 化学式: C₄₀H₄₆N₄O₂
• 分子量: 614.831
• InChiKey: DTWUYAWUJZLGBV-OGBHYEAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  bis((8S,9R)-6'-methoxycinchonan-9-yl) 在 10% Pd on charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以95%的产率得到bis((8S,9R)-6'-methoxy-10,11-dihydrocinchonan-9-yl)
  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：

  (8alpha,9R)-9-氯-6'-甲氧基脱氧辛可宁 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以55%的产率得到bis((8S,9R)-6'-methoxycinchonan-9-yl)
  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

文献信息

• Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New <i>C</i>₂-Symmetric Dimers
  作者：Przemysław J. Boratyński、Ilona Turowska-Tyrk、Jacek Skarżewski

  DOI：10.1021/jo801205n

  日期：2008.9.19

  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.