propenoic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester | 1154062-15-3

• 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)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester
• 英文别名: [(1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl] prop-2-enoate
• CAS: 1154062-15-3
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: BDGJCNNQXMMGSV-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  propenoic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester 、 环戊二烯 在 二甲基氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.52h， 生成 bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester 、 bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester
  参考文献：
  名称：

  Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2009.02.004
• 作为产物：
  描述：

  (1R,2S)-1-(2-methoxyethoxy)-1,2-bis-(2-methoxyphenyl)-ethanol 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以74%的产率得到propenoic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester
  参考文献：
  名称：

  Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2009.02.004

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.