(S)-2-trifluoroacetylamino-4-oxo-4-phenyl-butanoic acid | 200730-99-0

• 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: (S)-2-trifluoroacetylamino-4-oxo-4-phenyl-butanoic acid
• 英文别名: (2S)-4-oxo-4-phenyl-2-[(2,2,2-trifluoroacetyl)amino]butanoic acid
• CAS: 200730-99-0
• 化学式: C₁₂H₁₀F₃NO₄
• 分子量: 289.211
• InChiKey: RGFFVHICWSNKLG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-trifluoroacetylamino-4-oxo-4-phenyl-butanoic acid 在 1,1-二氯甲醚 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 (3S,5S,5aR)-(+/-)-3-trifluoroacetylamino-5-hydroxy-5-phenyl-1-aza-bicyclo<4.2.0>octan-2-one
  参考文献：
  名称：

  Synthesis of ornithine lactams via diastereoselective photocyclization of 2-amino-4-oxo-4-phenyl-butanoyl amines

  摘要：

  The diastereoselective synthesis of ornithine lactams 6-9 via photoinduced E-hydrogen abstraction followed by cyclization of the corresponding 1,6-biradicals is described. A highly asymmetric 1,4-induction is observed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00472-8
• 作为产物：
  描述：

  (S)-(-)-2-(三氟乙酰胺)琥珀酸酐 、 苯 在 三氯化铝 作用下， 生成 (S)-2-trifluoroacetylamino-4-oxo-4-phenyl-butanoic 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

• Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel–Crafts reaction with trifluoromethanesulfonic acid
  作者：Ryo Murashige、Yuka Hayashi、Makoto Hashimoto

  DOI：10.1016/j.tetlet.2008.09.013

  日期：2008.11

  reaction of TFA-Asp(Cl)-OMe and stoichiometric amounts of benzene was established by using neat trifluoromethanesulfonic acid (TfOH) as solvent and catalyst under a mild condition. This methodology has been applied to many aromatic compounds and enabled synthesis of several homophenylalanine derivatives.

  通过在温和条件下使用纯三氟甲磺酸（TfOH）作为溶剂和催化剂，可以建立TFA-Asp（Cl）-OMe与化学计量的苯的有效Friedel-Crafts反应。该方法已经应用于许多芳族化合物，并能够合成几种高苯丙氨酸衍生物。
• 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。