(2R,3S)-3-benzyloxy-2-[(2R)-2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine | 1171136-82-5

• 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: (2R,3S)-3-benzyloxy-2-[(2R)-2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine
• 英文别名: 3-[(2R)-2-hydroxy-3-[(2R,3S)-3-phenylmethoxypiperidin-2-yl]propyl]quinazolin-4-one
• CAS: 1171136-82-5
• 化学式: C₂₃H₂₇N₃O₃
• 分子量: 393.486
• InChiKey: SQUVKXZYQBWWTK-QIJUGHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2R,3S)-3-benzyloxy-2-[(2R)-2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以80%的产率得到(2R,3S)-N-(tert-butoxycarbonyl)-3-(benzyloxy)-2-[(2S)-2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine
  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
• 作为产物：
  描述：

  (2R,3aR,4S)-4-(benzyloxy)-2-[(4-oxo-4H-quinazolin-3-yl)methyl]hexahydroisoxazolo[2,3-a]pyridine 在 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 以53%的产率得到(2R,3S)-3-benzyloxy-2-[(2R)-2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine
  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.