(1S,2S,5R,1'R)-1-epoxyethyl-2-iso-propyl-5-methylcyclohexan-1-ol | 367939-65-9

• 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: (1S,2S,5R,1'R)-1-epoxyethyl-2-iso-propyl-5-methylcyclohexan-1-ol
• CAS: 367939-65-9
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: PXHJLRFVXGXDHQ-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二乙胺 、 (1S,2S,5R,1'R)-1-epoxyethyl-2-iso-propyl-5-methylcyclohexan-1-ol 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以19%的产率得到(1S,2S,5R,1'R)-1-(2'-N,N-diethylamino-1'-hydroxyethyl)-2-iso-propyl-5-methylcyclohexan-1-ol
  参考文献：
  名称：

  Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LICH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00206-3
• 作为产物：
  描述：

  (1R,2S,5R)-1-vinyl-2-iso-propyl-5-methylcyclohexan-1-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 27.0h， 以81%的产率得到(1S,2S,5R,1'R)-1-epoxyethyl-2-iso-propyl-5-methylcyclohexan-1-ol
  参考文献：
  名称：

  Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LICH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00206-3