propenoic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester | 1154062-14-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: propenoic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester
• 英文别名: [(1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl] prop-2-enoate
• CAS: 1154062-14-2
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: SMYXKLOGHLBFNJ-XZOQPEGZSA-N

物化性质

• 沸点：
  488.9±45.0 °C(predicted)
• 密度：
  1.088±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  propenoic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester 、 N-benzyliden-α-phenyl-glycine methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4S,5R)-2,5-diphenylpyrrolidine-2,4-dicarboxylic acid 4-[(1R,2S)-1,2-di(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl] ester 2-methyl ester 、 (2S,4R,5S)-2,5-diphenylpyrrolidine-2,4-dicarboxylic acid 4-[(1R,2S)-1,2-di(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl] ester 2-methyl ester
  参考文献：
  名称：

  Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides

  摘要：

  The metal-catalyzed stereoselective 1,3-dipolar cycloaddition of azomethine ylides and acrylates using recyclable meso-hydrobenzoin-derived chiral auxiliaries is described. Cleavage of the auxiliary leads to highly substituted pyrrolidines in up to 87% enantiomeric excess. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.010
• 作为产物：
  描述：

  (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethanol 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 propenoic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester
  参考文献：
  名称：

  Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides

  摘要：

  The metal-catalyzed stereoselective 1,3-dipolar cycloaddition of azomethine ylides and acrylates using recyclable meso-hydrobenzoin-derived chiral auxiliaries is described. Cleavage of the auxiliary leads to highly substituted pyrrolidines in up to 87% enantiomeric excess. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.010

文献信息

• Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses
  作者：Joachim Broeker、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2009.02.004

  日期：2009.2

  The applicability of five aryl substituted m-hydrobenzoin ethers already tested in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates as open chain chiral auxiliaries was further investigated via the alpha-alkylation of propionates, the addition of n-BuZnCl to phenylglyoxylates and the Diels-Alder reaction of acrylates with cyclopentadiene as model reactions. As up to 90% cle could be achieved in the solution phase, two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliaries in the same type of reactions. (C) 2009 Elsevier Ltd. All rights reserved.
• Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides
  作者：Katharina Bica、Peter Gaertner

  DOI：10.1016/j.tetasy.2010.04.010

  日期：2010.4

  The metal-catalyzed stereoselective 1,3-dipolar cycloaddition of azomethine ylides and acrylates using recyclable meso-hydrobenzoin-derived chiral auxiliaries is described. Cleavage of the auxiliary leads to highly substituted pyrrolidines in up to 87% enantiomeric excess. (C) 2010 Elsevier Ltd. All rights reserved.