6-(4-(4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoyl)piperazin-1-yl)-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1562520-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(4-(4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoyl)piperazin-1-yl)-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• CAS: 1562520-72-2
• 化学式: C₅₇H₅₇N₇O₅
• 分子量: 920.123
• InChiKey: GLSOIFXLEBWTPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.69
• 重原子数：
  69.0
• 可旋转键数：
  12.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100.19
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-(4-(4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoyl)piperazin-1-yl)-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 2.0h， 以77%的产率得到2-(6-(4-(4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoyl)piperazin-1-yl)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N,N,N-trimethylethanaminium
  参考文献：
  名称：

  Ground-State Elevation Approach To Suppress Side Reactions in Gold-Sensing Systems Based on Alkyne Activation

  摘要：

  A novel approach to suppress the side reactions observed in the reaction-based gold-sensing systems based on the alkyne activation is disclosed. By elevating steric strain around the reaction site, the gold ion promoted ring-opening process in rhodamine-lactam probes is significantly accelerated, which also leads to suppression of those possible side reactions. As a result, the probes show very high sensitivity in addition to excellent selectivity toward gold species. Furthermore, bioimaging of gold species in live cells was demonstrated with a FRET version.

  DOI：

  10.1021/ol5001389
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 甲醇 、 乙醇 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 125.5h， 生成 6-(4-(4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoyl)piperazin-1-yl)-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Ground-State Elevation Approach To Suppress Side Reactions in Gold-Sensing Systems Based on Alkyne Activation

  摘要：

  A novel approach to suppress the side reactions observed in the reaction-based gold-sensing systems based on the alkyne activation is disclosed. By elevating steric strain around the reaction site, the gold ion promoted ring-opening process in rhodamine-lactam probes is significantly accelerated, which also leads to suppression of those possible side reactions. As a result, the probes show very high sensitivity in addition to excellent selectivity toward gold species. Furthermore, bioimaging of gold species in live cells was demonstrated with a FRET version.

  DOI：

  10.1021/ol5001389