N-benzoyl dimethyl ester of (S)-α-[(E)-2-pentenyl]-aspartic acid

• 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: N-benzoyl dimethyl ester of (S)-α-[(E)-2-pentenyl]-aspartic acid
• 英文别名: dimethyl (2S)-2-benzamido-2-[(E)-pent-2-enyl]butanedioate
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: NMYVDRDKKBIPOR-YXOJNZSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-2-戊烯 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 73.0h， 生成 N-benzoyl dimethyl ester of (S)-α-[(E)-2-pentenyl]-aspartic acid
  参考文献：
  名称：

  Enantioselective synthesis of β-amino acids. Part 10: Preparation of novel α,α- and β,β-disubstituted β-amino acids from (S)-asparagine

  摘要：

  Perhydropyrimidinone (S)-1 is alkylated with very high diastereoselectivity to give trans products (2S,5R)-3, (2S,5R)-4 and (2S,5R)-5. Dialkylation of (S)-1 also proceeds with complete stereoselectivity to afford adducts (2S,5R)-6, (2S,5S)-6, (2S,5R)-7 and (2S,5S)-7. Hydrolysis (6N HCl, 100 degrees C) of monoalkylated derivative (2S,5R)-3 gives enantiopure alpha-substituted beta-amino acid (R)-8. Hydrolysis of dialkylated adducts 6 and 7 affords enantiopure alpha,alpha-disubstituted beta-amino acids (R)- or (S)-9 and (R)- or (S)-10. Related iminoester (2S,6S)-2 is alkylated with complete diastereoselectivity to give products (2S,6S)-11-13 whose hydrolysis under relatively mild conditions (2N CF3CO2H, CH3OH, 100 degrees C) affords enantiopure N-benzoylated beta,beta-disubstituted beta-amino acid esters (S)-14-16, with intact double bonds in the olefinic substituents. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00328-6

文献信息

• Enantioselective synthesis of β-amino acids. Part 10: Preparation of novel α,α- and β,β-disubstituted β-amino acids from (S)-asparagine
  作者：Eusebio Juaristi、Margarita Balderas、Heraclio López-Ruiz、Vı́ctor Manuel Jiménez-Pérez、Marı́a Luisa Kaiser-Carril、Yara Ramı́rez-Quirós

  DOI：10.1016/s0957-4166(99)00328-6

  日期：1999.9

  Perhydropyrimidinone (S)-1 is alkylated with very high diastereoselectivity to give trans products (2S,5R)-3, (2S,5R)-4 and (2S,5R)-5. Dialkylation of (S)-1 also proceeds with complete stereoselectivity to afford adducts (2S,5R)-6, (2S,5S)-6, (2S,5R)-7 and (2S,5S)-7. Hydrolysis (6N HCl, 100 degrees C) of monoalkylated derivative (2S,5R)-3 gives enantiopure alpha-substituted beta-amino acid (R)-8. Hydrolysis of dialkylated adducts 6 and 7 affords enantiopure alpha,alpha-disubstituted beta-amino acids (R)- or (S)-9 and (R)- or (S)-10. Related iminoester (2S,6S)-2 is alkylated with complete diastereoselectivity to give products (2S,6S)-11-13 whose hydrolysis under relatively mild conditions (2N CF3CO2H, CH3OH, 100 degrees C) affords enantiopure N-benzoylated beta,beta-disubstituted beta-amino acid esters (S)-14-16, with intact double bonds in the olefinic substituents. (C) 1999 Elsevier Science Ltd. All rights reserved.