allyl-N-cinnamoyl-L-proline-L-leucinate | 330636-85-6

• 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: allyl-N-cinnamoyl-L-proline-L-leucinate
• 英文别名: cinnamoyl(E)-Pro-Leu-Oallyl；prop-2-enyl (2S)-4-methyl-2-[[(2S)-1-[(E)-3-phenylprop-2-enoyl]pyrrolidine-2-carbonyl]amino]pentanoate
• CAS: 330636-85-6
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: CLOZIOVOJJTUPX-DSJWGCTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allyl-N-cinnamoyl-L-proline-L-leucinate 在 Grubbs catalyst first generation 、 polyaniline-supported Co(II) salen 氧气 、 异丁醛 、 cobalt(II) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 (Z)-(5S,6S,14S,16aS)-5-Hydroxy-14-isobutyl-7-(4-methoxy-phenyl)-6-phenyl-1,2,3,6,7,8,11,14,15,16a-decahydro-5H-12-oxa-3a,7,15-triaza-cyclopentacyclopentadecene-4,13,16-trione
  参考文献：
  名称：

  通过三肽的逆向诱导的闭环易位合成小环肽。

  摘要：

  可以在与Grubbs催化剂进行闭环复分解反应的过程中，对三肽1进行反向诱导（γ/β转向）环化反应，以形成相应的环状肽2。这些环状肽可能是有用的探针，可作为构象约束的生物活性模拟物结构相关的HIV蛋白酶抑制剂的构象。

  DOI：

  10.1021/jo0200320
• 作为产物：
  描述：

  3-溴丙烯 、 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以84%的产率得到allyl-N-cinnamoyl-L-proline-L-leucinate
  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

文献信息

• π-Facial selectivity in polyaniline supported cobalt catalysed aerobic epoxidation of N-cinnamoyl proline derivatives
  作者：E.N Prabhakaran、Jyoti Prokash Nandy、Shalini Shukla、Javed Iqbal

  DOI：10.1016/s0040-4039(00)01949-3

  日期：2001.1

  Polyaniline supported cobalt salen catalyses the facially selective aerobic epoxidation (oxygen/2-methylpropanal) of N-cinnamoyl proline derived peptides. A high diastereoselectivity is observed for peptides which are able to adopt a gamma- or beta -turn due to intramolecular hydrogen bonding. (C) 2000 Elsevier Science Ltd. Ail rights reserved.
• 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 of Small Cyclic Peptides via Reverse Turn Induced Ring Closing Metathesis of Tripeptides
  作者：E. N. Prabhakaran、I. Nageswara Rao、Anima Boruah、Javed Iqbal

  DOI：10.1021/jo0200320

  日期：2002.11.1

  A reverse turn induced (gamma/beta-turn) cyclization of tripeptides 1 can be performed in a ring closing metathesis reaction with Grubbs' catalyst to the corresponding cyclic peptides 2. These cyclic peptides may be useful probes as a conformationally constrained mimic of the bioactive conformation of structurally related HIV protease inhibitors.

  可以在与Grubbs催化剂进行闭环复分解反应的过程中，对三肽1进行反向诱导（γ/β转向）环化反应，以形成相应的环状肽2。这些环状肽可能是有用的探针，可作为构象约束的生物活性模拟物结构相关的HIV蛋白酶抑制剂的构象。