(8R,9R)-6'-methoxy-9-phenyl-cinchonan | 1007362-78-8

• 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: (8R,9R)-6'-methoxy-9-phenyl-cinchonan
• 英文别名: (9R)-9-deoxy-9-phenyl-quinidine；4-[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-phenylmethyl]-6-methoxyquinoline
• CAS: 1007362-78-8
• 化学式: C₂₆H₂₈N₂O
• 分子量: 384.521
• InChiKey: BNAZJSZFIPXMAN-TYTZFVCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9R)-6'-methoxy-9-phenyl-cinchonan 在 dimsylsodium 、 氧气 、 水 、 sodium hydrogensulfite 作用下， 以 二甲基亚砜 为溶剂， 反应 48.83h， 以21%的产率得到(8R,9S)-6'-methoxy-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
• 作为产物：
  描述：

  溴苯 、 9-epi-Chloroquinidine 在 magnesium 、 1,2-二溴乙烷 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 4.0h， 以60%的产率得到(8R,9R)-6'-methoxy-9-phenyl-cinchonan
  参考文献：
  名称：

  Stereoselective C9 Arylation and Vinylation of Cinchona Alkaloids

  摘要：

  A simple and efficient method for the highly stereoselective C-9 arylation and vinylation of Cinchona alkaloids was developed. Both 9s- and 9R-chloroquinine with PhMgBr yielded 9S-phenylquinine (X-ray structure). The reactions with various aryl and vinyl Grignard reagents resulted in the series of 9S-aryl and vinyl alkaloid derivatives. The stereochemical outcome was rationalized by coordination of the magnesium atom to the quinuclidine nitrogen, thus directing the nucleophilic attack at the C-9 stereogenic center.

  DOI：

  10.1021/ol7026625

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.
• Stereoselective C9 Arylation and Vinylation of <i>Cinchona</i> Alkaloids
  作者：Przemysław J. Boratyński、Ilona Turowska-Tyrk、Jacek Skarżewski

  DOI：10.1021/ol7026625

  日期：2008.2.1

  A simple and efficient method for the highly stereoselective C-9 arylation and vinylation of Cinchona alkaloids was developed. Both 9s- and 9R-chloroquinine with PhMgBr yielded 9S-phenylquinine (X-ray structure). The reactions with various aryl and vinyl Grignard reagents resulted in the series of 9S-aryl and vinyl alkaloid derivatives. The stereochemical outcome was rationalized by coordination of the magnesium atom to the quinuclidine nitrogen, thus directing the nucleophilic attack at the C-9 stereogenic center.