(8S,9S)-6'-methoxy-9-vinyl-cinchonan | 1007362-86-8

• 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: (8S,9S)-6'-methoxy-9-vinyl-cinchonan
• 英文别名: 4-[(1S)-1-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]prop-2-enyl]-6-methoxyquinoline
• CAS: 1007362-86-8
• 化学式: C₂₂H₂₆N₂O
• 分子量: 334.461
• InChiKey: RBDTZYKHJMVCBD-LYNVYRENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烯基溴化镁 、 (8alpha,9R)-9-氯-6'-甲氧基脱氧辛可宁 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到(8S,9S)-6'-methoxy-9-vinyl-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

• 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.