{(S)-1-[(S)-1-(3-Bromo-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester | 862839-00-7

• 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: {(S)-1-[(S)-1-(3-Bromo-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• CAS: 862839-00-7
• 化学式: C₂₇H₃₆BrN₃O₄
• 分子量: 546.505
• InChiKey: BDOUPJGEZASWGD-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  {(S)-1-[(S)-1-(3-Bromo-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 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
• 作为产物：
  描述：

  N-{[(2-甲基-2-丙基)氧基]羰基}苯丙氨酰亮氨酸甲酯 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 {(S)-1-[(S)-1-(3-Bromo-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-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