{1-[1-(3-bromo-benzylcarbamoyl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester | 862839-03-0

• 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: {1-[1-(3-bromo-benzylcarbamoyl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester
• CAS: 862839-03-0
• 化学式: C₂₁H₃₂BrN₃O₄
• 分子量: 470.407
• InChiKey: QOJUVWJBAPOUPE-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  96.53
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {1-[1-(3-bromo-benzylcarbamoyl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester 在 偶氮二异丁腈 三正丁基氢锡 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 19.0h， 生成 (5S,8S)-5-methyl-8-(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：

  (N-(tert-butoxycarbonyl)-L-leucinyl)-L-alanine methyl ester 在 lithium hydroxide 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 {1-[1-(3-bromo-benzylcarbamoyl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester
  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 Conformationally Constrained Cyclic Peptides Using an Intramolecular Sonogashira Coupling
  作者：V. Balraju、D. Srinivasa Reddy、Mariappan Periasamy、Javed Iqbal

  DOI：10.1021/jo051412z

  日期：2005.11.1

  [GRAPHICS]Small peptides having a 3-bromobenzyl group at the C-termini and n-alkynoyl group at the N-termini undergo a smooth copper-free intramolecular Sonogashira coupling reaction to afford the corresponding cyclic peptides in moderate yields. Scope and limitations of this macrocyclization is demonstrated with di-, tri-, and tetrapeptides.