(3-methyl-4-{6-[1-(2-nitrophenyl)ethoxy]-3-oxo-3H-xanthen-9-yl}phenoxy)acetic acid benzyl ester | 942948-74-5

• 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: (3-methyl-4-{6-[1-(2-nitrophenyl)ethoxy]-3-oxo-3H-xanthen-9-yl}phenoxy)acetic acid benzyl ester
• CAS: 942948-74-5
• 化学式: C₃₇H₂₉NO₈
• 分子量: 615.639
• InChiKey: YTJDNTHKOOLCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.04
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118.11
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3-methyl-4-{6-[1-(2-nitrophenyl)ethoxy]-3-oxo-3H-xanthen-9-yl}phenoxy)acetic acid benzyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以49%的产率得到(3-methyl-4-{6-[1-(2-nitrophenyl)ethoxy]-3-oxo-3H-xanthen-9-yl}phenoxy)acetic acid
  参考文献：
  名称：

  Highly Activatable and Rapidly Releasable Caged Fluorescein Derivatives

  摘要：

  Caged fluorophores, which recover fluorescence activity upon brief illumination with ultraviolet (UV) light, have played an important role in investigating cell lineage and cellular protein dynamics. In this paper, we report novel nitrobenzyl-caged fluorescein derivatives, based on our TokyoGreen platform (caged TokyoGreen), which have a single photoremovable protecting group, and the fluorescence quantum efficiency can be finely controlled via the photoinduced electron-transfer process before and after photoactivation. These new derivatives can be activated more rapidly and show a larger fluorescence enhancement than a traditional caged fluorescein, which is a bis-caged lactone form, upon brief UV irradiation both in the biological application and in cuvette experiments.

  DOI：

  10.1021/ja070376d
• 作为产物：
  描述：

  4-溴-3-甲基苯酚 在 咪唑 、 盐酸 、 叔丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 29.0h， 生成 (3-methyl-4-{6-[1-(2-nitrophenyl)ethoxy]-3-oxo-3H-xanthen-9-yl}phenoxy)acetic acid benzyl ester
  参考文献：
  名称：

  Highly Activatable and Rapidly Releasable Caged Fluorescein Derivatives

  摘要：

  Caged fluorophores, which recover fluorescence activity upon brief illumination with ultraviolet (UV) light, have played an important role in investigating cell lineage and cellular protein dynamics. In this paper, we report novel nitrobenzyl-caged fluorescein derivatives, based on our TokyoGreen platform (caged TokyoGreen), which have a single photoremovable protecting group, and the fluorescence quantum efficiency can be finely controlled via the photoinduced electron-transfer process before and after photoactivation. These new derivatives can be activated more rapidly and show a larger fluorescence enhancement than a traditional caged fluorescein, which is a bis-caged lactone form, upon brief UV irradiation both in the biological application and in cuvette experiments.

  DOI：

  10.1021/ja070376d