cinnamoyl(E)-Pro-Azi(Ph)-OEt | 475640-21-2

• 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: cinnamoyl(E)-Pro-Azi(Ph)-OEt
• 英文别名: ethyl (2S,3R)-3-phenyl-1-[(2S)-1-[(E)-3-phenylprop-2-enoyl]pyrrolidine-2-carbonyl]aziridine-2-carboxylate
• CAS: 475640-21-2
• 化学式: C₂₅H₂₆N₂O₄
• 分子量: 418.492
• InChiKey: LJIQNHVBHFLPPA-WBUBEJSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cinnamoyl(E)-Pro-Azi(Ph)-OEt 在 polyaniline supported cobalt(II) salen 氧气 、 sodium acetate 、 异丁醛 作用下， 以 乙腈 为溶剂， 以92%的产率得到ethyl (2S,3R)-3-phenyl-1-[(2S)-1-(3-phenyloxirane-2-carbonyl)pyrrolidine-2-carbonyl]aziridine-2-carboxylate
  参考文献：
  名称：

  Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of N-Cinnamoyl l-Proline Derived Peptides

  摘要：

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

  DOI：

  10.1021/jo020352j
• 作为产物：
  描述：

  ethyl (2S,3S)-3-azido-2-hydroxy-3-phenylpropanoate 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 cinnamoyl(E)-Pro-Azi(Ph)-OEt
  参考文献：
  名称：

  Stereoselective Synthesis of β-Substituted Phenylalanine-β-phenylisoserine-Derived Tripeptides Using N-Cinnamoyl-l-proline as Template:  Synthesis of Structural Analogues of HIV Protease Inhibitors

  摘要：

  N-Cinnamoyl-L-proline can be used as a template on which P-substituted phenylalanine and beta-phenylisoserine residues can be synthesized leading to tripeptide derivatives as structural analogues of HIV protease inhibitors.

  DOI：

  10.1021/jo0109826

文献信息

• Synthesis and conformation of proline containing tripeptides constrained with phenylalanine-like aziridine and dehydrophenylalanine residues
  作者：E.N. Prabhakaran、Jyoti Prokash Nandy、Shalini Shukla、Amit Tewari、Saibal Kumar Das、Javed Iqbal

  DOI：10.1016/s0040-4039(02)01236-4

  日期：2002.9

  Tripeptides containing proline and analogues of phenylalanine lead to the formation of beta-turn structures. The synthesis and beta-turn properties of four such compounds are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.