(S)-2-Acetylamino-4-oxo-4-phenyl-butyric acid | 200730-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-Acetylamino-4-oxo-4-phenyl-butyric acid
• 英文别名: (2S)-2-acetamido-4-oxo-4-phenylbutanoic acid
• CAS: 200730-91-2
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: ANFHHGZEHOVNHY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.47
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Acetylamino-4-oxo-4-phenyl-butyric acid 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 苯 为溶剂， 生成 (2S,3R,5S)-5-Acetylamino-3-hydroxy-1-methoxycarbonylmethyl-6-oxo-3-phenyl-piperidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio- and stereoselective 1,6-photocyclization of aspartic acid-derived chiral γ-ketoamides

  摘要：

  Chiral cc-acylamino gamma-ketoamides 2 were irradiated and regioisomeric 1,6-cyclization products 3 and 4 obtained in high yields. Symmetrically N,N-disubstituted substrates 2a,b reacted diastereoselectively to give the all-cis products 3a,b in high yields. High 1,3-asymmetric induction was also observed for the unsymmetrically N,N-disubstituted 2d and 2e. The stereoselectivity of these reactions is discussed in terms of SOC-controlled spin inversion geometries. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00448-7
• 作为产物：
  描述：

  N-(2,5-二氧代氧杂戊环-3-基)乙酰胺 、 苯 在 三氯化铝 作用下， 生成 (S)-2-Acetylamino-4-oxo-4-phenyl-butyric acid
  参考文献：
  名称：

  Regio- and stereoselective 1,6-photocyclization of aspartic acid-derived chiral γ-ketoamides

  摘要：

  Chiral cc-acylamino gamma-ketoamides 2 were irradiated and regioisomeric 1,6-cyclization products 3 and 4 obtained in high yields. Symmetrically N,N-disubstituted substrates 2a,b reacted diastereoselectively to give the all-cis products 3a,b in high yields. High 1,3-asymmetric induction was also observed for the unsymmetrically N,N-disubstituted 2d and 2e. The stereoselectivity of these reactions is discussed in terms of SOC-controlled spin inversion geometries. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00448-7

文献信息

• A Simple Approach to β-Amino Acids by Acylation of Arenes with N-Acyl Aspartic Anhydrides
  作者：Axel Griesbeck、Heike Heckroth

  DOI：10.1055/s-1997-1007

  日期：1997.11

  Friedel-Crafts acylation of arenes (benzene, toluene, o-xylene) with N-protected (Bz, Ac, Ac-Bn, Ts, Tfac, N,N-Pht) aspartic anhydrides (1a-1f) resulted in mixtures of α- and β-amino acids. The β/α-selectivity could be optimized for alkylated arenes (toluene, xylene) and the N-Ac, N-Bn protected 1c.

  用 N 保护（Bz、Ac、Ac-Bn、Ts、Tfac、N,N-Pht）的天冬氨酸酐（1a-1f）对炔类化合物（苯、甲苯、邻二甲苯）进行 Friedel-Crafts酰化反应，可得到δ-和²-氨基酸的混合物。δ/δ选择性可通过烷基化的茴香（甲苯、二甲苯）和 N-Ac、N-Bn 保护的 1c 得到优化。
• Regio- and stereoselective 1,6-photocyclization of aspartic acid-derived chiral γ-ketoamides
  作者：Axel G. Griesbeck、Heike Heckroth、Hans Schmickler

  DOI：10.1016/s0040-4039(99)00448-7

  日期：1999.4

  Chiral cc-acylamino gamma-ketoamides 2 were irradiated and regioisomeric 1,6-cyclization products 3 and 4 obtained in high yields. Symmetrically N,N-disubstituted substrates 2a,b reacted diastereoselectively to give the all-cis products 3a,b in high yields. High 1,3-asymmetric induction was also observed for the unsymmetrically N,N-disubstituted 2d and 2e. The stereoselectivity of these reactions is discussed in terms of SOC-controlled spin inversion geometries. (C) 1999 Elsevier Science Ltd. All rights reserved.