(S)-2-amino-3-phenyl-N-propylpropanamide | 35373-94-5

• 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-amino-3-phenyl-N-propylpropanamide
• 英文别名: (2S)-2-amino-3-phenyl-N-propylpropanamide
• CAS: 35373-94-5
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: GURZATZWEMIWEC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-3-phenyl-N-propylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.81h， 以86%的产率得到(S)-3-phenyl-N1-phenylpropane-1,2-diamine
  参考文献：
  名称：

  通过使用新型的伯-仲二胺催化剂，将丙二酸酯有机催化的高对映选择性的丙二酸迈克尔加成反应。

  摘要：

  DOI：

  10.1002/chem.200801749
• 作为产物：
  描述：

  L-苯丙氨酸 在 氢气 、 N,N'-二环己基碳二亚胺 作用下， 生成 (S)-2-amino-3-phenyl-N-propylpropanamide
  参考文献：
  名称：

  Synthesis of Chiral Tropopodands Having L-Amino Acid Moieties and Ability of Their Metal Complexes as an Asymmetric Catalyst

  摘要：

  Optical active tropopodands (10 and 11) having neutral L-amino acids and L-histidine moieties were synthesized. Within their metal complexes, Pd complexes of histidine-tropopodands (11b and 11c) bearing bulky amide moieties showed good ability as an asymmetric catalyst in conjugate addition.

  DOI：

  10.3987/com-05-s(t)58

文献信息

• Structural insight into the aggregation of <scp>l</scp>-prolyl dipeptides and its effect on organocatalytic performance
  作者：Cristina Berdugo、Beatriu Escuder、Juan F. Miravet

  DOI：10.1039/c4ob02003k

  日期：——

  NMR and organocatalytic studies of four dipeptides derived from l-proline are described.

  NMR和有机催化研究了从L-脯氨酸衍生的四个二肽。
• Amino Acids and Peptides. VI. Novel Peptide Bond Formation catalyzed by Metal Ions. IV. Formation of optically Active Amino Acid Amides and Peptide Amides
  作者：MITSUYOSHI WAGATSUMA、SHIRO TERASHIMA、SHUN-ICHI YAMADA

  DOI：10.1248/cpb.21.422

  日期：——

  The Cu (II)-catalyzed peptide bond formation previously reported by us, was applied to the synthesis of optically active amino acid amides and peptide amides. Treatment of an optically active amino acid ester with a primary amine in the presence of anhydrous CuCl2 afforded the desired amino acid secondary amide, without racemization, in 60-70% yield. However, the same reaction with a secondary amine with larger steric hindrance than primary amine gave an optically active tertiary amide in a very low yield as expected from the proposed mechanism. Almost all the amino acid amides could be isolated as hydrochlorides or as free bases. Some peptide amides, i. e. Z-Gly-Gly-NH-Bzl, and Z-Ala-Gly-NH-Bzl, were also prepared.

  我们之前报道的Cu(II)催化肽键形成反应，被应用于光学活性氨基酸酰胺和肽酰胺的合成。在无水CuCl2的存在下，将光学活性氨基酸酯与一级胺反应，可以获得所需的氨基酸次级酰胺，且未发生消旋化，产率为60-70%。然而，与具有比一级胺更大空间位阻的二级胺进行相同反应，根据提出的机理预期，得到的光学活性三级酰胺产率非常低。几乎所有的氨基酸酰胺都可以分离为盐酸盐形式或游离碱形式。一些肽酰胺，例如Z-Gly-Gly-NH-Bzl和Z-Ala-Gly-NH-Bzl，也被制备出来。
• Direct amidation of unprotected amino acids using B(OCH₂CF₃)₃
  作者：Rachel M. Lanigan、Valerija Karaluka、Marco T. Sabatini、Pavel Starkov、Matthew Badland、Lee Boulton、Tom D. Sheppard

  DOI：10.1039/c6cc05147b

  日期：——

  A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of [small alpha]-amino acids with a range of amines in cyclopentyl methyl ether. The method can...

  可商购的硼酸酯B（OCH 2 CF 3）3可用于在环戊基甲基醚中实现小α-氨基酸与一系列胺的无保护基的直接酰胺化。该方法可以...
• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010037533A1

  公开（公告）日：2010-04-08

  The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及喹啉衍生物及其药用盐。该发明还涉及一种制备这种化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此对于控制和预防各种疾病，包括神经系统疾病，非常有用。
• Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group in<i>N</i>-Protected Peptides under Mild Basic Conditions
  作者：Marta Tena-Solsona、César A. Angulo-Pachón、Beatriu Escuder、Juan F. Miravet

  DOI：10.1002/ejoc.201400154

  日期：2014.6

  protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilises the tetrahedral intermediate formed after nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N-protected tripeptides and tetrapeptides but Z-protected dipeptides are stable under the same conditions

  苄氧羰基 (Z) 保护基团在室温温和碱性条件下出乎意料的不稳定可通过基于嵌合辅助的机制来解释。发现邻酰胺基团稳定了在氢氧化物与 Z 基团的羰基亲核加成后形成的四面体中间体。这种效应在 N 保护的三肽和四肽中起作用，但 Z 保护的二肽在相同条件下是稳定的，因为邻位酰胺 NH 通过与末端羧酸根部分的分子内 H 键合而被阻断。