(2S,3R,4S)-2-(hydroxymethyl)-4-tetradecylpiperidin-3-ol | 1149373-11-4

• 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: (2S,3R,4S)-2-(hydroxymethyl)-4-tetradecylpiperidin-3-ol
• CAS: 1149373-11-4
• 化学式: C₂₀H₄₁NO₂
• 分子量: 327.551
• InChiKey: OWHRIQBBGAXYEN-SLFFLAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (8R,8aS)-3-oxo-7-((E)-tetradec-1-enyl)-3,5,8,8a-tetrahydro-1H-oxazolo[3,4-α]pyridin-8-yl acetate 在 氢气 、 镍 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.17h， 以100%的产率得到(2S,3R,4S)-2-(hydroxymethyl)-4-tetradecylpiperidin-3-ol
  参考文献：
  名称：

  Design and Synthesis of Piperidine-Containing Sphingoid Base Analogues

  摘要：

  We report an approach that allows the efficient synthesis of the designed sphingoid base analogues in which the conformational restriction is introduced by incorporation of a cyclic moiety between the 2-amino group and the C-4 carbon atom of the sphingoid base. Our synthesis features a tandem enyne/diene-ene metathesis reaction that provides access to the designed framework. The diene moiety of the metathesis product is stereoselectively elaborated for the synthesis of the designed analogues. The preliminary biological evaluation indicates that the designed constrained analogues are much more effective than prototype natural sphingoid bases at inhibiting cancer cell growth.

  DOI：

  10.1021/jo900378h

文献信息

• Design and Synthesis of Piperidine-Containing Sphingoid Base Analogues
  作者：Jihee Cho、Yun Mi Lee、Deukjoon Kim、Sanghee Kim

  DOI：10.1021/jo900378h

  日期：2009.5.15

  We report an approach that allows the efficient synthesis of the designed sphingoid base analogues in which the conformational restriction is introduced by incorporation of a cyclic moiety between the 2-amino group and the C-4 carbon atom of the sphingoid base. Our synthesis features a tandem enyne/diene-ene metathesis reaction that provides access to the designed framework. The diene moiety of the metathesis product is stereoselectively elaborated for the synthesis of the designed analogues. The preliminary biological evaluation indicates that the designed constrained analogues are much more effective than prototype natural sphingoid bases at inhibiting cancer cell growth.