(3S,5S)-1-allyl-4-dibenzylamino-3,5-dihydroxypiperidine | 1044272-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,5S)-1-allyl-4-dibenzylamino-3,5-dihydroxypiperidine
• 英文别名: (3S,5S)-4-(dibenzylamino)-1-prop-2-enylpiperidine-3,5-diol
• CAS: 1044272-87-8
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: BGCNZTTUARLHNB-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙烯胺 、 (-)-(2R,4R)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以90%的产率得到(3S,5S)-1-allyl-4-dibenzylamino-3,5-dihydroxypiperidine
  参考文献：
  名称：

  Totally Selective Synthesis of Enantiopure (3S,5S)- and (3R,5R)-4-Amino-3,5-dihydroxypiperidines from Aminodiepoxides Derived from Serine

  摘要：

  [GRAPHICS]The transformation of enantiopure (2R,4R)- and (2S,4S)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine, 1 and 2, into the corresponding enantiopure (3S,5S)- and (3R,5R)-3,5-dihydroxy-3-aminopiperidines, 3 and 4 respectively, is described. The opening of the two epoxide rings with a range of amines takes place with total regioselectivity and high yields, in the presence of LiClO4. A mechanism to explain this transformation is proposed.

  DOI：

  10.1021/jo801058c

文献信息

• Totally Selective Synthesis of Enantiopure (3<i>S</i>,5<i>S</i>)- and (3<i>R</i>,5<i>R</i>)-4-Amino-3,5-dihydroxypiperidines from Aminodiepoxides Derived from Serine
  作者：José M. Concellón、Ignacio A. Rivero、Humberto Rodríguez-Solla、Carmen Concellón、Estibaly España、Santiago García-Granda、M. R. Díaz

  DOI：10.1021/jo801058c

  日期：2008.8.1

  [GRAPHICS]The transformation of enantiopure (2R,4R)- and (2S,4S)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine, 1 and 2, into the corresponding enantiopure (3S,5S)- and (3R,5R)-3,5-dihydroxy-3-aminopiperidines, 3 and 4 respectively, is described. The opening of the two epoxide rings with a range of amines takes place with total regioselectivity and high yields, in the presence of LiClO4. A mechanism to explain this transformation is proposed.