2-oxopropionic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester

• 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: 2-oxopropionic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester
• 英文别名: [(1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl] 2-oxopropanoate
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: XFUIFUFSQVTQIJ-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-oxopropionic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester 、 4-甲基-4-戊烯基溴 在 magnesium 、 甲醇 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 (R)-2-hydroxy-2,6-dimethylhept-6-enoic acid, (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester 、
  参考文献：
  名称：

  Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin

  摘要：

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.016
• 作为产物：
  描述：

  (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethanol 、 丙酮酸 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-oxopropionic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester
  参考文献：
  名称：

  Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin

  摘要：

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.016

文献信息

• Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin
  作者：Christian Schuster、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2006.08.016

  日期：2006.9

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.