(2S,3aS,4S)-4-(benzyloxy)-2-[(4-oxo-4H-quinazolin-3-yl)methyl]hexahydroisoxazolo[2,3-a]pyridine | 1171136-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (2S,3aS,4S)-4-(benzyloxy)-2-[(4-oxo-4H-quinazolin-3-yl)methyl]hexahydroisoxazolo[2,3-a]pyridine
• 英文别名: 3-[[(2S,3aS,4S)-4-phenylmethoxy-3,3a,4,5,6,7-hexahydro-2H-[1,2]oxazolo[2,3-a]pyridin-2-yl]methyl]quinazolin-4-one
• CAS: 1171136-81-4
• 化学式: C₂₃H₂₅N₃O₃
• 分子量: 391.47
• InChiKey: LCLFATLTFSJYKO-NYVOZVTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-allylquinazolin-4(3H)-one 、 (3S)-3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide 以 甲苯 为溶剂， 以48%的产率得到(2R,3aR,4S)-4-(benzyloxy)-2-[(4-oxo-4H-quinazolin-3-yl)methyl]hexahydroisoxazolo[2,3-a]pyridine
  参考文献：
  名称：

  Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine

  摘要：

  A study into the synthesis and synthetic utility of (S)-3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide is described. This nitrone is readily accessed from L-glutamic acid and the regio- and stereoselectivity of cycloaddition of this compound with a range of alkenes has been probed. Reductive cleavage of the major cycloadducts provides access to a diverse range of trans-2,3-disubstituted piperidines. The synthetic scope of this nitrone is further illustrated by the use of this compound as a key intermediate in a concise synthesis of the anti-malarial agent (+)-febrifugine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.044

文献信息

• Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine
  作者：Amir Ashoorzadeh、Glenn Archibald、Vittorio Caprio

  DOI：10.1016/j.tet.2009.04.044

  日期：2009.6

  A study into the synthesis and synthetic utility of (S)-3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide is described. This nitrone is readily accessed from L-glutamic acid and the regio- and stereoselectivity of cycloaddition of this compound with a range of alkenes has been probed. Reductive cleavage of the major cycloadducts provides access to a diverse range of trans-2,3-disubstituted piperidines. The synthetic scope of this nitrone is further illustrated by the use of this compound as a key intermediate in a concise synthesis of the anti-malarial agent (+)-febrifugine. (C) 2009 Elsevier Ltd. All rights reserved.