(S)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol | 1221590-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol
• 英文别名: (S)-cyclohexyl(1-methoxymethylcyclohexyl)methanol；(S)-cyclohexyl-[1-(methoxymethyl)cyclohexyl]methanol
• CAS: 1221590-23-3
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: QORSZAAOXPHKEX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (S)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol 在 碘代三甲硅烷 、 sodium iodide 作用下， 以 四氯化碳 为溶剂， 以47%的产率得到(S)-cyclohexyl(1-(hydroxymethyl)cyclohexyl)methanol
  参考文献：
  名称：

  Acid-catalyzed aldol-Meerwein–Ponndorf–Verley-etherification reactions—access to defined configured quaternary stereogenic centers

  摘要：

  A novel asymmetric aldol-reduction-etherification process of aliphatic enolizable aldehydes is described. The intermediately formed aldol adducts-beta-hydroxyaldehydes-were reduced and transformed into the corresponding 1,3-diol ethers by external secondary alcohols at the same time. Thus, with the help of chiral secondary alcohols an access to optically active 1,3-diol ether is given. Furthermore, asymmetric cross-aldol-Meerwein-Ponndorf reactions of enolizable aldehydes can also be realized under these reaction conditions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.069
• 作为产物：
  描述：

  甲醇 、 环己烷基甲醛 在 lithium perchlorate 、 (-)-menthol trimethylsilyl ether 、 三氟乙酸 作用下， 反应 2.0h， 生成 (R)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol 、 (S)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol
  参考文献：
  名称：

  Asymmetric Acid-Catalyzed Meerwein−Ponndorf−Verley−Aldol Reactions of Enolizable Aldehydes

  摘要：

  A highly, stereo- and regioselective Meerwein - Ponndorf - Verley - Aldol etherification process of enolizable aldehydes is described. This new transformation is catalyzed by trifluoroacetic acid. The method also allows cross-aldol reactions with alpha-branched enolizable aldehydes and thus provides access to defined configured quaternary stereogenic centers.

  DOI：

  10.1021/ol100093u