(2R,3S)-2-benzyl-1-methoxy-5-phenylpentan-3-ol | 1221590-25-5

• 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: (2R,3S)-2-benzyl-1-methoxy-5-phenylpentan-3-ol
• CAS: 1221590-25-5
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: MEIVAVXIEFMNFB-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (2R,3S)-2-benzyl-1-methoxy-5-phenylpentan-3-ol 在 碘代三甲硅烷 、 对甲苯磺酸 、 sodium iodide 作用下， 以 四氯化碳 为溶剂， 生成
  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：

  苯丙醛 、 甲醇 在 lithium perchlorate 、 (-)-menthol trimethylsilyl ether 、 三氟乙酸 作用下， 反应 2.0h， 生成 (2RS,3RS)-2-benzyl-1-methoxy-5-phenylpentan-3-ol 、 (2R,3S)-2-benzyl-1-methoxy-5-phenylpentan-3-ol
  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.
• 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.