(S)-2-amino-4-(4-((pyren-1-ylmethyl)carbamoyl)-1H-1,2,3-triazol-1-yl)butanoic acid | 1428675-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (S)-2-amino-4-(4-((pyren-1-ylmethyl)carbamoyl)-1H-1,2,3-triazol-1-yl)butanoic acid
• CAS: 1428675-30-2
• 化学式: C₂₄H₂₁N₅O₃
• 分子量: 427.462
• InChiKey: ABSGBYGLSDCNGG-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  123.13
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-(pyren-1-ylmethyl)propiolamide 、 (2S)-2-氨基-4-叠氮基丁烷酸 在 copper(II) sulfate 、 三(3-羟丙基三唑甲基)胺 作用下， 生成 (S)-2-amino-4-(4-((pyren-1-ylmethyl)carbamoyl)-1H-1,2,3-triazol-1-yl)butanoic acid
  参考文献：
  名称：

  Relative Performance of Alkynes in Copper-Catalyzed Azide–Alkyne Cycloaddition

  摘要：

  Copper-catalyzed azide-alkyne cycloaddition (CuAAC) has found numerous applications in a variety of fields. We report here only modest differences in the reactivity of various classes of terminal alkynes under typical bioconjugative and preparative organic conditions. Propargyl compounds represent an excellent combination of azide reactivity, ease of installation, and cost. Electronically activated propiolamides are slightly more reactive, at the expense of increased propensity for Michael addition. Certain alkynes, including tertiary propargyl carbamates, are not suitable for bioconjugation due to copper-induced fragmentation. A fluorogenic probe based on such reactivity is available in one step from rhodamine 110 and can be useful for optimization of CuAAC conditions.

  DOI：

  10.1021/bc300672b