(5S,7R,8R)-2-phenyl-8-methoxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline N-oxide | 1048030-69-8

• 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: (5S,7R,8R)-2-phenyl-8-methoxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline N-oxide
• 英文别名: (1S,8R,9R)-8-methoxy-10,10-dimethyl-6-oxido-5-phenyl-6-azoniatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
• CAS: 1048030-69-8
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: XHKDJILKAWGBRX-RVKKMQEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (5S,7R,8R)-2-phenyl-8-methoxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到(5S,7R,8R)-2-phenyl-8-methoxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline N-oxide
  参考文献：
  名称：

  Chiral pyridine N-oxides derived from monoterpenes as organocatalysts for stereoselective reactions with allyltrichlorosilane and tetrachlorosilane

  摘要：

  The synthesis of enantiomerically pure C-2-symmetric dipyridylmethane ligands and related N,N'-dioxides is reported. A procedure for the synthesis of a few new enantiomerically pure C-2-symmetric pyridine N-oxides and the preparation of four pyridine N-oxides with oxygen and nitrogen atoms as further coordinating elements in the heterocycle framework is described. All compounds were prepared from naturally occurring monoterpenes. These new compounds were assessed as organocatalysts in two different reactions, namely the allylation of aldehydes with allyltrichlorosilane that afforded homoallylic alcohols in good yields and up to 85% ee and the stilbene oxide opening by the addition of tetrachlorosilane that gave chlorohydrin in quantitative yield and up to 70% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.105