N-(2-(4-(6-amino-9-ethyl-9H-purine-8-yl)-1H-1,2,3-triazol-1-yl)acetyl)-2-benzyloxycarbonylamino-3-methylbutanamide | 1454891-33-8

• 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: N-(2-(4-(6-amino-9-ethyl-9H-purine-8-yl)-1H-1,2,3-triazol-1-yl)acetyl)-2-benzyloxycarbonylamino-3-methylbutanamide
• CAS: 1454891-33-8
• 化学式: C₂₄H₂₈N₁₀O₄
• 分子量: 520.551
• InChiKey: TYHUSCLZUYIGHC-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  184.83
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(2-(4-(6-amino-9-ethyl-9H-purine-8-yl)-1H-1,2,3-triazol-1-yl)acetyl)-2-benzyloxycarbonylamino-3-methylbutanamide 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 0.42h， 以22%的产率得到2-amino-N-(2-(4-(6-amino-9-ethyl-9H-purine-8-yl)-1H-1,2,3-triazol-1-yl)acetyl)-3-methylbutanamide
  参考文献：
  名称：

  Synthesis and photophysical characterization of 1- and 4-(purinyl)triazoles

  摘要：

  Fluorescent adenine mimetics are useful tools for studying DNA, RNA and enzyme functions. Herein we describe the synthesis of eight 1-(purinyl)triazoles and two 4-(purinyl)triazoles utilizing the 1,4-regioselective copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction as the key step. The fluorescence properties of five of the synthesized 1-(purinyl)triazoles are also presented. The five measured compounds displayed low quantum yields. The results, when compared to previously published data, suggest a high influence of the substitution pattern of the triazole on the fluorescence properties. (c) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.023
• 作为产物：
  描述：

  8-bromo-9-ethyladenine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 33.08h， 生成 N-(2-(4-(6-amino-9-ethyl-9H-purine-8-yl)-1H-1,2,3-triazol-1-yl)acetyl)-2-benzyloxycarbonylamino-3-methylbutanamide
  参考文献：
  名称：

  Synthesis and photophysical characterization of 1- and 4-(purinyl)triazoles

  摘要：

  Fluorescent adenine mimetics are useful tools for studying DNA, RNA and enzyme functions. Herein we describe the synthesis of eight 1-(purinyl)triazoles and two 4-(purinyl)triazoles utilizing the 1,4-regioselective copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction as the key step. The fluorescence properties of five of the synthesized 1-(purinyl)triazoles are also presented. The five measured compounds displayed low quantum yields. The results, when compared to previously published data, suggest a high influence of the substitution pattern of the triazole on the fluorescence properties. (c) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.023