cinnamoyl(E)-Pro-Phe(a,b-dehydro)-Leu-OMe | 330637-00-8

• 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-Phe(a,b-dehydro)-Leu-OMe
• 英文别名: methyl (2S)-4-methyl-2-[[(Z)-3-phenyl-2-[[(2S)-1-[(E)-3-phenylprop-2-enoyl]pyrrolidine-2-carbonyl]amino]prop-2-enoyl]amino]pentanoate
• CAS: 330637-00-8
• 化学式: C₃₀H₃₅N₃O₅
• 分子量: 517.625
• InChiKey: JZDIORRVHXSVJU-UKBLQAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cinnamoyl(E)-Pro-Phe(a,b-dehydro)-Leu-OMe 在 polyaniline supported cobalt(II) salen 、 氧气 、 异丁醛 作用下， 以 乙腈 为溶剂， 以89%的产率得到(S)-4-Methyl-2-((Z)-3-phenyl-2-{[(S)-1-((2R,3S)-3-phenyl-oxiranecarbonyl)-pyrrolidine-2-carbonyl]-amino}-acryloylamino)-pentanoic acid methyl ester
  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：

  N-cinnamoyl-(L)-proline 在 lithium hydroxide 、 碘代三甲硅烷 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 、 水 为溶剂， 生成 cinnamoyl(E)-Pro-Phe(a,b-dehydro)-Leu-OMe
  参考文献：
  名称：

  Synthesis and conformation of proline containing tripeptides constrained with phenylalanine-like aziridine and dehydrophenylalanine residues

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)01236-4

文献信息

• Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of <i>N</i>-Cinnamoyl <scp>l</scp>-Proline Derived Peptides
  作者：Jyoti Prokosh Nandy、E. N. Prabhakaran、S. Kiran Kumar、A. C. Kunwar、Javed Iqbal

  DOI：10.1021/jo020352j

  日期：2003.3.1

  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.
• 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.