(3R,4S)-3-(methoxymethyl)-2,6-dimethylheptan-4-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1221590-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4S)-3-(methoxymethyl)-2,6-dimethylheptan-4-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1221590-49-3
• 化学式: C₂₁H₃₁F₃O₄
• 分子量: 404.47
• InChiKey: MEEYXFFXMUAAEY-BJLQDIEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  异戊醛 在 4-二甲氨基吡啶 、 lithium perchlorate 、 (-)-menthol trimethylsilyl ether 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (3R,4S)-3-(methoxymethyl)-2,6-dimethylheptan-4-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  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

文献信息

• Asymmetric Acid-Catalyzed Meerwein−Ponndorf−Verley−Aldol Reactions of Enolizable Aldehydes
  作者：Andrea Seifert、Ulf Scheffler、Morris Markert、Rainer Mahrwald

  DOI：10.1021/ol100093u

  日期：2010.4.16

  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.