(1S,2R,5R)-2-(1-hydroxyethyl)-2,5-dimethylcyclohexanol | 212559-34-7

• 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,2R,5R)-2-(1-hydroxyethyl)-2,5-dimethylcyclohexanol
• 英文别名: (1S,2S,5R)-2-[(1R)-1-hydroxyethyl]-2,5-dimethylcyclohexan-1-ol
• CAS: 212559-34-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: QPGOIZBVYCNQJH-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酮 、 (1S,2R,5R)-2-(1-hydroxyethyl)-2,5-dimethylcyclohexanol 在 对甲苯磺酸 作用下， 生成 (4R,4aS,7R,8aS)-2,2,4,4a,7-Pentamethyl-hexahydro-benzo[1,3]dioxine
  参考文献：
  名称：

  Stereoselective Reductive Rearrangement of α-Hydroxy Epoxides:  A New Method for Synthesis of 1,3-Diols¹

  摘要：

  A novel and short synthetic method for the stereoselective synthesis of 1,3-diols has been developed by an unusual reductive rearrangement of a series of cl-hydroxy epoxides with aluminum isopropoxide. The reaction process was also investigated with deuterium-labeled aluminum isopropoxide, which revealed a site-specific 1,2-carbon-to-carbon migration and successive stereoselective hydride shift. The main synthetically valuable feature is that up to three contiguous carbon centers, the C-1, C-2, and C-3, were stereoselectively controlled with C-2 being quaternary. This reaction is of particular importance to the synthesis of newly developed powerful asymmetric hydrogenation catalysts containing the chiral ligands of spirocyclic diols.

  DOI：

  10.1021/jo981097z
• 作为产物：
  描述：

  (4R)-1-(1-hydroxy-1-methylethyl)-4-methylcyclohexene 在 aluminum isopropoxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 10.0h， 生成 (1S,2R,5R)-2-(1-hydroxyethyl)-2,5-dimethylcyclohexanol
  参考文献：
  名称：

  Stereoselective Reductive Rearrangement of α-Hydroxy Epoxides:  A New Method for Synthesis of 1,3-Diols¹

  摘要：

  A novel and short synthetic method for the stereoselective synthesis of 1,3-diols has been developed by an unusual reductive rearrangement of a series of cl-hydroxy epoxides with aluminum isopropoxide. The reaction process was also investigated with deuterium-labeled aluminum isopropoxide, which revealed a site-specific 1,2-carbon-to-carbon migration and successive stereoselective hydride shift. The main synthetically valuable feature is that up to three contiguous carbon centers, the C-1, C-2, and C-3, were stereoselectively controlled with C-2 being quaternary. This reaction is of particular importance to the synthesis of newly developed powerful asymmetric hydrogenation catalysts containing the chiral ligands of spirocyclic diols.

  DOI：

  10.1021/jo981097z