(E,1S)-7-[tert-butyl(dimethyl)silyl]oxy-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-3-prop-2-enylhept-2-en-1-ol | 1151796-88-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,1S)-7-[tert-butyl(dimethyl)silyl]oxy-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-3-prop-2-enylhept-2-en-1-ol
• CAS: 1151796-88-1
• 化学式: C₂₆H₅₀O₂Si
• 分子量: 422.767
• InChiKey: BCZZQZUYUHNMHW-QHZAGLBLSA-N

物化性质

• 沸点：
  473.6±45.0 °C(predicted)
• 密度：
  0.893±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,1S)-7-[tert-butyl(dimethyl)silyl]oxy-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-3-prop-2-enylhept-2-en-1-ol 在 copper(l) iodide 、 氧气 、 N,N-二异丙基乙胺 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以72%的产率得到(4E)-8-[tert-butyl(dimethyl)silyl]oxy-4-[(2S)-2-hydroxy-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]ethylidene]octan-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-Euphococcinine and (−)-Adaline

  摘要：

  We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.

  DOI：

  10.1021/jo9001992
• 作为产物：
  描述：

  tert-butyl-[(5E)-5-(iodomethylidene)oct-7-enoxy]-dimethylsilane 、 p-menthane-3-carboxaldehyde 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 17.5h， 以66%的产率得到(E,1S)-7-[tert-butyl(dimethyl)silyl]oxy-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-3-prop-2-enylhept-2-en-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-Euphococcinine and (−)-Adaline

  摘要：

  We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.

  DOI：

  10.1021/jo9001992

文献信息

• Stereoselective Synthesis of (+)-Euphococcinine and (−)-Adaline
  作者：Mélissa Arbour、Stéphanie Roy、Cédrickx Godbout、Claude Spino

  DOI：10.1021/jo9001992

  日期：2009.5.15

  We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.