2(S)-benzyl-3(S)-aminobutanoic acid | 139344-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2(S)-benzyl-3(S)-aminobutanoic acid
• 英文别名: (2S,3S)-3-amino-2-benzylbutanoic acid
• CAS: 139344-70-0
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: MPZATBABDVMQAB-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2(S)-benzyl-3(S)-aminobutanoic acid 在 盐酸 作用下， 反应 30.0h， 生成 [R-(R*,R*)]-α-(1-aminoethyl)benzenepropanoic acid.
  参考文献：
  名称：

  Enzymatic Resolution of α-Alkyl β-Amino Acids Using Immobilized Penicillin G Acylase

  摘要：

  DOI：

  10.1021/jo9613500
• 作为产物：
  描述：

  1-benzoyl-2(R)-tert-butyl-3,6(S)-dimethyl-5(S)-benzylperhydropyrimidin-4-one 在 盐酸 作用下， 反应 6.0h， 以89%的产率得到2(S)-benzyl-3(S)-aminobutanoic acid
  参考文献：
  名称：

  Enantioselective synthesis of .beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl- and 2-benzyl-3-aminobutanoic acid

  摘要：

  An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported. From 2a, the four possible stereisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3. In the cyclization of 3, the cis products 4 predominate ca. 95.5. These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6). Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.

  DOI：

  10.1021/jo00034a037

文献信息

• Diastereoselektive Alkylierung von 3-Aminobutansäure in der 2-Stellung
  作者：Heinrich Estermann、Dieter Seebach

  DOI：10.1002/hlca.19880710724

  日期：1988.11.2

  Diastereoselective Alkylation 3-Aminobutanoic Acid in the 2-Position

  2位非对映选择性烷基化3-氨基丁酸
• Diastereoselective synthesis of β-amino acid derivatives from dihydropyridones
  作者：Markus Ege、Klaus T. Wanner

  DOI：10.1016/j.tet.2008.05.073

  日期：2008.7

  A new method for the diastereoselective preparation of stereoisomeric 2,3-disubstituted β-amino acids is presented. It is based on trans- and cis-2,3-disubstituted dihydropyridones, which were derived from 2-monosubstituted N-acyl dihydropyridone derivatives. Alkylation of the enolates of 2-substituted dihydropyridones gave trans-2,3-disubstituted dihydropyridones with high diastereoselectivities.

  提出了一种非对映选择性制备立体异构体2,3-二取代的β-氨基酸的新方法。它是基于反式-和顺-2,3-二取代的二氢吡啶，将其衍生自2单取代Ñ酰基二氢吡啶酮衍生物。2-取代的二氢吡啶酮的烯醇盐的烷基化得到具有高非对映选择性的反式-2,3-二取代的二氢吡啶酮。通过去质子化/再质子化序列使二氢吡啶酮核的C-3处的立体中心反转，从而以高收率和非对映选择性产生了立体异构体顺式-2,3-二取代的二氢吡啶酮。除去N之后-酰基保护基团，高碘酸钠分别氧化生成的顺式或反式-2,3-异位二氢吡啶酮，导致相应的非对映体β-氨基酸氧化降解。
• Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid
  作者：Eusebio Juaristi、Jaime Escalante

  DOI：10.1021/jo00060a051

  日期：1993.4

  The title perhydropyrimidin-4-one (S)-4 was prepared from (S)-3-aminobutanoic acid via the Schiff base (S)-8. This heterocycle was alkylated (LDA, methyl iodide, or benzyl bromide) to afford the like and unlike diastereomeric products in a 80:20 ratio. Separation and hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free, enantiomerically pure, amino acids 11-14.
• Enzymatic Resolution of α-Alkyl β-Amino Acids Using Immobilized Penicillin G Acylase
  作者：Giuliana Cardillo、Alessandra Tolomelli、Claudia Tomasini

  DOI：10.1021/jo9613500

  日期：1996.1.1
• Enantioselective synthesis of .beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl- and 2-benzyl-3-aminobutanoic acid
  作者：Eusebio Juaristi、Jaime Escalante、Bernd Lamatsch、Dieter Seebach

  DOI：10.1021/jo00034a037

  日期：1992.4

  An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported. From 2a, the four possible stereisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3. In the cyclization of 3, the cis products 4 predominate ca. 95.5. These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6). Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.