2-[(2R,3S)-1-benzyl-3-(benzyloxy)piperidin-2-yl]ethan-1-ol | 1171136-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-[(2R,3S)-1-benzyl-3-(benzyloxy)piperidin-2-yl]ethan-1-ol
• CAS: 1171136-69-8
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: QJCGJLMIIUFGSW-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[(2R,3S)-1-benzyl-3-(benzyloxy)piperidin-2-yl]ethan-1-ol 在 10% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以100%的产率得到2-[(2R,3S)-3-(benzyloxy)piperidin-2-yl]ethan-1-ol
  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)-2-ethoxy-4-(benzyloxy)-hexahydroisoxazolo[2,3-a]pyridine 、 溴甲苯 在 lithium aluminium tetrahydride 、 水 、 rochelle salt 作用下， 以 二氯甲烷 、 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 12.0h， 以59%的产率得到2-[(2R,3S)-1-benzyl-3-(benzyloxy)piperidin-2-yl]ethan-1-ol
  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.