11(S)-methylnopol | 90701-47-6

• 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: 11(S)-methylnopol
• 英文别名: (2S)-1-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]propan-2-ol
• CAS: 90701-47-6
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: MRBHKGCTZZIBOV-LSJOCFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  beta-pinene 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 11(S)-methylnopol
  参考文献：
  名称：

  Asymmetric reductions of prochiral ketones with lithium [2-[2-benzyloxy)ethyl]-6,6-dimethylbicyclo[3.1.1]-3-nonyl]-9-boratabicyclo-[3.3.1]nonane (lithium NB-Enantride) and its derivatives

  摘要：

  NB-Enantride, prepared by hydroboration of nopyl benzyl ether with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by treatment with tert-butyllithium, is an effective asymmetric reducing agent. Especially noteworthy is the fact that it can reduce aliphatic ketones such as 2-octanone or 2-butanone in efficiencies approaching 80% enantiomeric excess. Several analogues have been tested in order to probe the structural features which contribute to making this reagent effective. The ether group evidently plays a role in obtaining high selectivity, since changing oxygen to nitrogen or sulfur causes a drop in selectivity. Moving the ether group by one atom in either direction or making it more hindered causes a drop in selectivity. However, replacing the OCH2C6H5 group with a methyl group also results in an effective reducing agent and suggests that steric factors play an important role. The lithium cation was also found to be very important. Whereas the lithium compound reduced acetophenone within minutes at -78-degrees-C, the potassium analogue gave no reduction over an extended period. At higher temperatures (-65-degrees-C) reduction did slowly occur with the potassium compound, but the selectivity was greatly reduced in comparison to the lithium compound.

  DOI：

  10.1021/jo00003a030