[1-(3-bromo-benzylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester | 869959-33-1

• 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-(3-bromo-benzylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: [1-(3-bromobenzylcarbamoyl)ethyl]carbamic acid tert-butyl ester；tert-butyl N-[(2S)-1-[(3-bromophenyl)methylamino]-1-oxopropan-2-yl]carbamate
• CAS: 869959-33-1
• 化学式: C₁₅H₂₁BrN₂O₃
• 分子量: 357.247
• InChiKey: NVQCOEPIXNOPJV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-(3-bromo-benzylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-Amino-N-((S)-1-{(S)-1-[(S)-1-(3-bromo-benzylcarbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-2-phenyl-ethyl)-benzamide
  参考文献：
  名称：

  Synthesis of Cyclic Peptides Constrained with Biarylamine Linkers Using Buchwald−Hartwig C−N Coupling

  摘要：

  In this paper, we describe the synthesis of conformationally constrained cyclic peptides with biarylamine linkers for peptidomimetics using palladium-catalyzed intramolecular Buchwald-Hartwig C-N coupling. We have prepared a variety of di-, tri-, and tetrapeptides (16-22-membered) in good yields using this reaction.

  DOI：

  10.1021/jo061366i
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 3-溴苄胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以87%的产率得到[1-(3-bromo-benzylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Conformationally Constrained Cyclic Peptides Using an Intramolecular Sonogashira Coupling

  摘要：

  [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.

  DOI：

  10.1021/jo051412z

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.
• Synthesis of Cyclic Peptides Constrained with Biarylamine Linkers Using Buchwald−Hartwig C−N Coupling
  作者：V. Balraju、Javed Iqbal

  DOI：10.1021/jo061366i

  日期：2006.11.1

  In this paper, we describe the synthesis of conformationally constrained cyclic peptides with biarylamine linkers for peptidomimetics using palladium-catalyzed intramolecular Buchwald-Hartwig C-N coupling. We have prepared a variety of di-, tri-, and tetrapeptides (16-22-membered) in good yields using this reaction.