(8R,9S)-9-phenyl-9-cinchonanol | 1393601-67-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (8R,9S)-9-phenyl-9-cinchonanol
• 英文别名: 9-phenylcinchonine；(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-phenyl-quinolin-4-ylmethanol
• CAS: 1393601-67-6
• 化学式: C₂₅H₂₆N₂O
• 分子量: 370.494
• InChiKey: UDPNWBSLVYMXID-XDESJKQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛可宁 在 magnesium 作用下， 以 乙醚 为溶剂， 生成 (8R,9S)-9-phenyl-9-cinchonanol 、
  参考文献：
  名称：

  Synthetic approaches to 9-arylated Cinchona alkaloids: stereoselective addition of Grignard reagents to cinchonanones and hydroxylation of 9-phenylcinchonanes

  摘要：

  All 8,9-isomers of the 9-phenyl Cinchona alkaloids were obtained by autoxidation of 9-deoxy-9-phenyl-alkaloids and by the addition of Grignard reagents to the respective ketones. The diastereoselective addition of phenyl-, methyl-, and vinylmagnesium reagents to quinidinone and cinchoninone gave the corresponding (8R,9S)-products with acceptable yields and starting material recovery. The configurations of the compounds obtained were established by chemical correlations, NMR experiments, and were supported by DFT calculations and X-ray structures. Stereochemical models for both reactions were also devised and discussed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.024

文献信息

• Synthetic approaches to 9-arylated Cinchona alkaloids: stereoselective addition of Grignard reagents to cinchonanones and hydroxylation of 9-phenylcinchonanes
  作者：Przemysław J. Boratyński、Ilona Turowska-Tyrk、Jacek Skarżewski

  DOI：10.1016/j.tetasy.2012.05.024

  日期：2012.6

  All 8,9-isomers of the 9-phenyl Cinchona alkaloids were obtained by autoxidation of 9-deoxy-9-phenyl-alkaloids and by the addition of Grignard reagents to the respective ketones. The diastereoselective addition of phenyl-, methyl-, and vinylmagnesium reagents to quinidinone and cinchoninone gave the corresponding (8R,9S)-products with acceptable yields and starting material recovery. The configurations of the compounds obtained were established by chemical correlations, NMR experiments, and were supported by DFT calculations and X-ray structures. Stereochemical models for both reactions were also devised and discussed. (c) 2012 Elsevier Ltd. All rights reserved.