(2S)-N-[(3-bromophenyl)methyl]-4-methyl-2-[[(2S)-3-phenyl-2-(prop-2-enoylamino)propanoyl]amino]pentanamide | 862839-09-6

• 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: (2S)-N-[(3-bromophenyl)methyl]-4-methyl-2-[[(2S)-3-phenyl-2-(prop-2-enoylamino)propanoyl]amino]pentanamide
• CAS: 862839-09-6
• 化学式: C₂₅H₃₀BrN₃O₃
• 分子量: 500.435
• InChiKey: DVDHIKANVSYEMF-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-N-[(3-bromophenyl)methyl]-4-methyl-2-[[(2S)-3-phenyl-2-(prop-2-enoylamino)propanoyl]amino]pentanamide 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 15.0h， 以47%的产率得到(5S,8S)-8-benzyl-5-(2-methylpropyl)-3,6,9-triazabicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-4,7,10-trione
  参考文献：
  名称：

  Synthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization

  摘要：

  In this letter, we report that small peptides (di- and tri-) having a 3-bromobenzyl group at the C-termini and an acryloyl group at the N-termini undergo an efficient Bu3SnH-AlBN mediated intramolecular free radical cyclization to afford cyclic peptides in good yields. We also propose that these cyclizations are occurring via a pre-organized acyclic structure dictated by a reverse turn (gamma/beta-turn). (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.05.115
• 作为产物：
  描述：

  alpha-叔丁氧羰基-L-苯丙氨酰-L-亮氨酸 在 三乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S)-N-[(3-bromophenyl)methyl]-4-methyl-2-[[(2S)-3-phenyl-2-(prop-2-enoylamino)propanoyl]amino]pentanamide
  参考文献：
  名称：

  Synthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization

  摘要：

  In this letter, we report that small peptides (di- and tri-) having a 3-bromobenzyl group at the C-termini and an acryloyl group at the N-termini undergo an efficient Bu3SnH-AlBN mediated intramolecular free radical cyclization to afford cyclic peptides in good yields. We also propose that these cyclizations are occurring via a pre-organized acyclic structure dictated by a reverse turn (gamma/beta-turn). (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.05.115

文献信息

• Synthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization
  作者：V. Balraju、D. Srinivasa Reddy、Mariappan Periasamy、Javed Iqbal

  DOI：10.1016/j.tetlet.2005.05.115

  日期：2005.8

  In this letter, we report that small peptides (di- and tri-) having a 3-bromobenzyl group at the C-termini and an acryloyl group at the N-termini undergo an efficient Bu3SnH-AlBN mediated intramolecular free radical cyclization to afford cyclic peptides in good yields. We also propose that these cyclizations are occurring via a pre-organized acyclic structure dictated by a reverse turn (gamma/beta-turn). (c) 2005 Published by Elsevier Ltd.