(8R,9S)-9-azido-(9-deoxy)epiquinidine | 286460-05-7

• 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,9S)-9-azido-(9-deoxy)epiquinidine
• 英文别名: 4-[(S)-azido-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methyl]-6-methoxyquinoline
• CAS: 286460-05-7
• 化学式: C₂₀H₂₃N₅O
• 分子量: 349.436
• InChiKey: OUXQZBYQVPSMLR-LHHVKLHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  39.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8R,9S)-9-azido-(9-deoxy)epiquinidine 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

  摘要：

  Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids. (C) 2013 Xue-Bing Ma and Ming Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.008
• 作为产物：
  描述：

  在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 生成 (8R,9S)-9-azido-(9-deoxy)epiquinidine
  参考文献：
  名称：

  An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

  摘要：

  Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids. (C) 2013 Xue-Bing Ma and Ming Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.008

文献信息

• Clickable 9-azido-(9-deoxy)-Cinchona alkaloids: synthesis and conformation
  作者：Karol Kacprzak、Błażej Gierczyk

  DOI：10.1016/j.tetasy.2010.10.023

  日期：2010.11

  The synthesis and conformational preferences of 9-azido-(9-deoxy)-Cinchona alkaloids constituting a novel class of Cinchona alkaloid derivatives of both natural and 9-epi configurations are described One and two-step preparative syntheses of 9-azido-(9-deoxy)-Cinchona alkaloids have been developed allowing for their easy access on a multigram scale The stereochemical integrity of these azides has been confirmed from their circular dichroism and specific rotation data The conformations of the 9-azido Cinchona alkaloids deduced from both H-1 NMR and DFT calculations show that this class of Cinchona derivatives largely reflect the conformational preferences of the corresponding Cinchona bases this strategy therefore offers a defined chiral and clickable scaffold (C) 2010 Elsevier Ltd All rights reserved