4-(6-Hydroxy-3-oxo-3H-xanthen-9-YL)-3-methoxybenzoic acid | 876752-74-8

• 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-(6-Hydroxy-3-oxo-3H-xanthen-9-YL)-3-methoxybenzoic acid
• 英文别名: 4-(3-hydroxy-6-oxoxanthen-9-yl)-3-methoxybenzoic acid
• CAS: 876752-74-8
• 化学式: C₂₁H₁₄O₆
• 分子量: 362.339
• InChiKey: CYCIIHUVLAFEML-UHFFFAOYSA-N

物化性质

• 沸点：
  687.5±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(6-Hydroxy-3-oxo-3H-xanthen-9-YL)-3-methoxybenzoic acid 、 叔丁醇 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 反应 2.0h， 以79%的产率得到Tert-butyl 4-(3-hydroxy-6-oxoxanthen-9-yl)-3-methoxybenzoate
  参考文献：
  名称：

  Creation of Superior Carboxyfluorescein Dyes by Blocking Donor-Excited Photoinduced Electron Transfer

  摘要：

  Carboxyfluoresceins are widely utilized as fluorescence labeling reagents, but we recently found that their emission intensity is markedly decreased after esterification. On the basis of our hypothesis that the fluorescence decrease is due to a donor- excited photoinduced electron transfer (d- PeT) process, we have developed novel carboxyfluorescein derivatives in which the d- PeT process is hampered, and the emission intensity is not decreased upon esterification. These novel dye derivatives display high quantum yields and are expected to be useful as labeling agents.

  DOI：

  10.1021/ol0623926
• 作为产物：
  描述：

  4-溴-3-甲氧基苯甲酸 在 4-二甲氨基吡啶 、 sodium hydroxide 、 叔丁基锂 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 4-(6-Hydroxy-3-oxo-3H-xanthen-9-YL)-3-methoxybenzoic acid
  参考文献：
  名称：

  Creation of Superior Carboxyfluorescein Dyes by Blocking Donor-Excited Photoinduced Electron Transfer

  摘要：

  Carboxyfluoresceins are widely utilized as fluorescence labeling reagents, but we recently found that their emission intensity is markedly decreased after esterification. On the basis of our hypothesis that the fluorescence decrease is due to a donor- excited photoinduced electron transfer (d- PeT) process, we have developed novel carboxyfluorescein derivatives in which the d- PeT process is hampered, and the emission intensity is not decreased upon esterification. These novel dye derivatives display high quantum yields and are expected to be useful as labeling agents.

  DOI：

  10.1021/ol0623926

文献信息

• Creation of Superior Carboxyfluorescein Dyes by Blocking Donor-Excited Photoinduced Electron Transfer
  作者：Tomoko Mineno、Tasuku Ueno、Yasuteru Urano、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ol0623926

  日期：2006.12.1

  Carboxyfluoresceins are widely utilized as fluorescence labeling reagents, but we recently found that their emission intensity is markedly decreased after esterification. On the basis of our hypothesis that the fluorescence decrease is due to a donor- excited photoinduced electron transfer (d- PeT) process, we have developed novel carboxyfluorescein derivatives in which the d- PeT process is hampered, and the emission intensity is not decreased upon esterification. These novel dye derivatives display high quantum yields and are expected to be useful as labeling agents.