(1R)-1-cyclohexyl-3-methoxy-2,2-dimethylpropan-1-ol | 1356864-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-cyclohexyl-3-methoxy-2,2-dimethylpropan-1-ol
• CAS: 1356864-38-4
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: ANUUIPFSNDMNCK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  甲醇 、 异丁醛 、 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 (1R)-1-cyclohexyl-3-methoxy-2,2-dimethylpropan-1-ol 、 (1S)-1-cyclohexyl-3-methoxy-2,2-dimethylpropan-1-ol
  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

文献信息

• Acid-catalyzed aldol-Meerwein–Ponndorf–Verley-etherification reactions—access to defined configured quaternary stereogenic centers
  作者：Andrea Seifert、Kerstin Rohr、Rainer Mahrwald

  DOI：10.1016/j.tet.2011.11.069

  日期：2012.1

  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.