(S)-N-benzoyl-valine anilide | 29618-28-8

• 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: (S)-N-benzoyl-valine anilide
• 英文别名: N-benzoyl-(S)-valine anilide；N-Benzoyl-L-valin-anilid；Benzoyl-L-valin-anilid；N-benzoyl-L-valine anilide；N-[(2S)-1-anilino-3-methyl-1-oxobutan-2-yl]benzamide
• CAS: 29618-28-8
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: GBLLLYQYPOEYIH-INIZCTEOSA-N

物化性质

• 熔点：
  220-221 °C
• 沸点：
  560.3±33.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-benzoyl-valine anilide 在 sodium tetrahydroborate 、 碘 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

  摘要：

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.020
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 palladium on activated charcoal 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 5.0h， 生成 (S)-N-benzoyl-valine anilide
  参考文献：
  名称：

  Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

  摘要：

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.020

文献信息

• A Study of the Strength of a Template Molecule—A Functional Monomer Interaction That Affects the Performance of Molecularly Imprinted Polymers and Its Application to Chiral Amplification
  作者：Takuro Yasuyama、Hirofumi Matsunaga、Shin Ando、Tadao Ishizuka

  DOI：10.1248/cpb.c16-00974

  日期：——

  molecularly imprinted polymer (MIP), N-benzoyl-(S)-valine anilide-imprinted polymer (IP-2), was prepared using hydrogen-bonding interactions as a main force in the pre-polymerization step. The performance of the IP-2 was evaluated via batch procedure and compared with a (S)-valine anilide-imprinted polymer (IP-1) that was prepared using an ionic interaction that is stronger than hydrogen bonding. Although both

  在预聚合步骤中，使用氢键相互作用作为主要力量，制备了一种新型的分子印迹聚合物（MIP），即N-苯甲酰基-（S）-缬氨酸苯胺印迹聚合物（IP-2）。IP-2的性能通过分批程序进行了评估，并与使用强于氢键的离子相互作用制备的（S）-缬氨酸苯胺印迹聚合物（IP-1）进行了比较。尽管两种聚合物均显示出对（S）-氨基酸衍生物的优先吸附性，但是在吸附性和对映选择性方面观察到不同的性能。另外，IP-2能够识别缬氨酸衍生的手性催化剂的对映异构体。这种现象被应用于手性扩增反应，
• Enzymic Synthesis of Peptide Bonds. III. The Relative Effects of Some Amino Acids and their Acyl Substituents¹
  作者：Sidney W. Fox、Harry Wax

  DOI：10.1021/ja01167a075

  日期：1950.11
• Doherty; Popenoe, Journal of Biological Chemistry, 1951, vol. 189, p. 447,458,459
  作者：Doherty、Popenoe

  DOI：——

  日期：——
• Maclaren et al., Australian Journal of Chemistry, 1958, vol. 11, p. 345,355
  作者：Maclaren et al.

  DOI：——

  日期：——
• Asymmetric Enzymatic Synthesis of Amino Acid Anilides
  作者：Noel F. Albertson

  DOI：10.1021/ja01145a144

  日期：1951.1