(8R,8aS,E)-8-hydroxy-7-(tetradec-1-enyl)-8,8a-dihydro-1H-oxazolo[3,4-α]pyridin-3(5H)-one | 1149373-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (8R,8aS,E)-8-hydroxy-7-(tetradec-1-enyl)-8,8a-dihydro-1H-oxazolo[3,4-α]pyridin-3(5H)-one
• 英文别名: (8R,8aS)-8-hydroxy-7-[(E)-tetradec-1-enyl]-1,5,8,8a-tetrahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 1149373-22-7
• 化学式: C₂₁H₃₅NO₃
• 分子量: 349.514
• InChiKey: SCFKJFJEEDXAQY-FGXJKGHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,8aS,E)-8-hydroxy-7-(tetradec-1-enyl)-8,8a-dihydro-1H-oxazolo[3,4-α]pyridin-3(5H)-one 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 0.17h， 以99%的产率得到(8R,8aS)-7-(3-dodecyloxiran-2-yl)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-α]pyridin-3(5H)-one
  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
• 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 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(8R,8aS,E)-8-hydroxy-7-(tetradec-1-enyl)-8,8a-dihydro-1H-oxazolo[3,4-α]pyridin-3(5H)-one
  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.