5,11-dimethoxy-1-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}dibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-8(1H)-one | 1407523-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,11-dimethoxy-1-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}dibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-8(1H)-one
• CAS: 1407523-40-3
• 化学式: C₂₆H₂₇N₃O₆
• 分子量: 477.517
• InChiKey: XMQAFVFVXMUGQI-MOBSCGTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.93
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  6,7-dibromo-4,9-dimethoxy-6,7-dihydro-1H-dibenzo[a,e]cyclopropa[c]cycloocten-1-one 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 5,11-dimethoxy-1-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}dibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-8(1H)-one
  参考文献：
  名称：

  A Fluorogenic Probe for the Catalyst-Free Detection of Azide-Tagged Molecules

  摘要：

  Fluorogenic reactions in which non- or weakly fluorescent reagents produce highly fluorescent products can be exploited to detect a broad range of compounds including biomolecules and materials. We describe a modified dibenzocyclooctine that under catalyst-free conditions undergoes fast strain promoted cycloadditions with azides to yield strongly fluorescent triazoles. The Cycloaddition products are more than 1000-fold brighter compared to the Starting cyclooctyne, exhibit large Stokes shift,. and can be excited above 350 nm, which is required for many applications. Quantum mechanical: calculations indicate that the fluorescence increase upon triazole formation is due to large differences in oscillator strengths of the S-0 <-> S-1 transitions in the planar C-2v-symmetric starting material compared to the symmetry broken and nonplanar.cycloaddition products. The new fluorogenic probe was successfully employed for labeling of proteins modified by an azide moiety.

  DOI：

  10.1021/ja309000s