4-[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-pyridin-2-ylpyridin-2-yl)oxymethyl]quinoline | 1446495-77-7

• 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: 4-[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-pyridin-2-ylpyridin-2-yl)oxymethyl]quinoline
• CAS: 1446495-77-7
• 化学式: C₂₉H₂₈N₄O
• 分子量: 448.568
• InChiKey: LYENEIWSKQSVKM-QVZIYMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  辛可宁 、 6-溴-2,2'-联吡啶 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以41%的产率得到4-[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-pyridin-2-ylpyridin-2-yl)oxymethyl]quinoline
  参考文献：
  名称：

  Modular bipyridine ligands coupled with Cinchona alkaloids for Cu(II)-catalyzed asymmetric Henry reactions

  摘要：

  A new series of bipyridine ligands coupled with Cinchona alkaloids were prepared in relatively high yields in only one step starting from commercially or readily available materials, and have been developed as chiral ligands for copper(II)-catalyzed asymmetric Henry reactions. The catalytic system works well with a wide range of aromatic, aliphatic, and heteroaromatic aldehydes to afford the corresponding nitroalkanols with high enantioselectivity (up to 92%) in good yields (up to 89%). A transition state model was proposed based on H-1 NMR spectroscopy, X-ray structure, and computational calculations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.009