(-)-(S)-1-((2R,3aS,4R,6aR)-3a-allyl-1,1,4-trimethyloctahydropentalen-2-yl)ethanol | 1176891-17-0

• 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: (-)-(S)-1-((2R,3aS,4R,6aR)-3a-allyl-1,1,4-trimethyloctahydropentalen-2-yl)ethanol
• CAS: 1176891-17-0
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: VKVFMDGUOWGCKR-BLDNINTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-(S)-1-((2R,3aS,4R,6aR)-3a-allyl-1,1,4-trimethyloctahydropentalen-2-yl)ethanol 、 甲苯磺酰氨基甲酸甲酯 在 air 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 N,N-二异丙基乙胺 、 对苯醌 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以81%的产率得到(-)-methyl(E)-3-((2R,3aS,4R,6aR)-2-((S)-1-hydroxyethyl)-1,1,4-trimethyloctahydropentalen-3a-yl)allyl(tosyl)carbamate
  参考文献：
  名称：

  A Catalytic, Brønsted Base Strategy for Intermolecular Allylic C−H Amination

  摘要：

  A Bronsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.

  DOI：

  10.1021/ja903939k

文献信息

• A Catalytic, Brønsted Base Strategy for Intermolecular Allylic C−H Amination
  作者：Sean A. Reed、Anthony R. Mazzotti、M. Christina White

  DOI：10.1021/ja903939k

  日期：2009.8.26

  A Bronsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.