(3R,4S,E)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-(tributylstannyl)dodec-1-en-3-ol | 1613336-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (3R,4S,E)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-(tributylstannyl)dodec-1-en-3-ol
• CAS: 1613336-97-2
• 化学式: C₃₃H₆₇NO₂Sn
• 分子量: 628.61
• InChiKey: YHLWRKXCRQPEGN-DNSLGMQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.39
• 重原子数：
  37.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (3R,4S,E)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-(tributylstannyl)dodec-1-en-3-ol 在 咪唑 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N,N-二异丙基乙胺 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 methyl (9R,10S,E)-6-oxo-10-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-9-((triethylsilyl)oxy)octadec-7-enoate
  参考文献：
  名称：

  anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense

  摘要：

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.

  DOI：

  10.1021/ol501263y
• 作为产物：
  描述：

  (E)-1,2-bis(tri-n-butylstannyl)ethene 、 2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)decanal 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以77.778%的产率得到
  参考文献：
  名称：

  anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense

  摘要：

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.

  DOI：

  10.1021/ol501263y