4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoicacid | 1562520-69-7

• 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: 4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoicacid
• CAS: 1562520-69-7
• 化学式: C₃₇H₃₅N₃O₄
• 分子量: 585.703
• InChiKey: LVXWNFDEFXHHIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(2-(dimethylamino)ethyl)-6-(piperazin-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 、 4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoicacid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以39 mg的产率得到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
• 作为产物：
  描述：

  4-amino-3-[2-(trimethylsilyl)ethynyl]benzoic acid 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 4-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)-3-ethynylbenzoicacid
  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