benzyl 2-[(tert-butoxycarbonyl)amino]-3-(5,11-dimethoxy-8-oxodibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-1(8H)-yl)propanoate | 1407523-46-9

• 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: benzyl 2-[(tert-butoxycarbonyl)amino]-3-(5,11-dimethoxy-8-oxodibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-1(8H)-yl)propanoate
• CAS: 1407523-46-9
• 化学式: C₃₄H₃₂N₄O₇
• 分子量: 608.651
• InChiKey: NKHMQLTXTZGVRU-MOFSIZSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  130.87
• 氢给体数：
  1.0
• 氢受体数：
  10.0

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 (R)-benzyl 2-[(tert-butoxycarbonyl)amino]-3-(5,11-dimethoxy-8-oxodibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-1(8H)-yl)propanoate 、 benzyl 2-[(tert-butoxycarbonyl)amino]-3-(5,11-dimethoxy-8-oxodibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-1(8H)-yl)propanoate
  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