9-(bromomethyl)-6-hydroxy-3H-xanthen-3-one*DDQ complex | 1392603-53-0

• 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: 9-(bromomethyl)-6-hydroxy-3H-xanthen-3-one*DDQ complex
• 英文别名: 9-(Bromomethyl)-6-hydroxyxanthen-3-one;4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile；9-(bromomethyl)-6-hydroxyxanthen-3-one;4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
• CAS: 1392603-53-0
• 化学式: C₈Cl₂N₂O₂*C₁₄H₉BrO₃
• 分子量: 532.134
• InChiKey: JBWDJSZAWRXVAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(bromomethyl)-6-hydroxy-3H-xanthen-3-one*DDQ complex 在 aq. phosphate buffer 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 6-hydroxy-9-methyl-3H-xanthen-3-one
  参考文献：
  名称：

  Fluorescein Analogues as Photoremovable Protecting Groups Absorbing at ∼520 nm

  摘要：

  A new photoremovable protecting group, (6-hydroxy-3-oxo-3H-xanthen-9-yl)methyl (1), with a molar absorption coefficient e of similar to 4 x 10(4) m(-1) cm(-1) at similar to 520 nm for the release of carboxylates or phosphates is reported. Three derivatives of 1 (diethyl phosphate, acetate, and bromide) were isolated as complexes with DDQ and shown to release the ligands with quantum yields <= 2.4% in aqueous solution.

  DOI：

  10.1021/jo301455n
• 作为产物：
  描述：

  (3,6-dimethoxy-9H-xanthen-9-yl)methanol 在 四溴化碳 、 三溴化硼 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 34.33h， 生成 9-(bromomethyl)-6-hydroxy-3H-xanthen-3-one*DDQ complex
  参考文献：
  名称：

  Fluorescein Analogues as Photoremovable Protecting Groups Absorbing at ∼520 nm

  摘要：

  A new photoremovable protecting group, (6-hydroxy-3-oxo-3H-xanthen-9-yl)methyl (1), with a molar absorption coefficient e of similar to 4 x 10(4) m(-1) cm(-1) at similar to 520 nm for the release of carboxylates or phosphates is reported. Three derivatives of 1 (diethyl phosphate, acetate, and bromide) were isolated as complexes with DDQ and shown to release the ligands with quantum yields <= 2.4% in aqueous solution.

  DOI：

  10.1021/jo301455n