6-hydroxy-3-oxo-3H-xanthene-9-carboxylic acid

• 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-hydroxy-3-oxo-3H-xanthene-9-carboxylic acid
• 英文别名: 6-hydroxy-3-oxo-3H-xanthene-9-carboxylic acid；6-Hydroxy-3-oxo-3H-xanthen-9-carbonsaeure；3-hydroxy-6-oxoxanthene-9-carboxylic acid
• 化学式: C₁₄H₈O₅
• 分子量: 256.215
• InChiKey: PTMZIRSRGUUSAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxy-3-oxo-3H-xanthene-9-carboxylic acid 生成 6-羟基-3-氧杂蒽-3-酮
  参考文献：
  名称：

  Fluorescein Analogue Xanthene-9-Carboxylic Acid: A Transition-Metal-Free CO Releasing Molecule Activated by Green Light

  摘要：

  6-Hydroxy-3-oxo-3H-xanthene-9-carboxylic acid is introduced as the first transition-metal-free carbon monoxide releasing molecule activated by visible light (photoCORM). This water-soluble fluorescein analogue releases carbon monoxide in both water and methanol upon irradiation at 500 nm. When selectively irradiated in the presence of hemoglobin (Hb) under physiological conditions, released CO is quantitatively trapped to form carboxyhemoglobin (COHb). The reaction progress can be accurately monitored by characteristic absorption and emission properties of the reactants and products.

  DOI：

  10.1021/ol4021089
• 作为产物：
  描述：

  (3,6-dimethoxy-9H-xanthen-9-yl)methanol 在 4-二甲氨基吡啶 、 三溴化硼 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.33h， 生成 6-hydroxy-3-oxo-3H-xanthene-9-carboxylic acid
  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

文献信息

• Sen; Sinha, Journal of the American Chemical Society, 1923, vol. 45, p. 2993
  作者：Sen、Sinha

  DOI：——

  日期：——
• Hewitt; Pope, Chemische Berichte, <hi>1896</hi>, vol. 29, p. 2825
  作者：Hewitt、Pope

  DOI：——

  日期：——
• US5972987A
  申请人：——

  公开号：US5972987A

  公开（公告）日：1999-10-26
• Fluorescein Analogues as Photoremovable Protecting Groups Absorbing at ∼520 nm
  作者：Peter Šebej、Jürgen Wintner、Pavel Müller、Tomáš Slanina、Jamaludin Al Anshori、Lovely Angel Panamparambil Antony、Petr Klán、Jakob Wirz

  DOI：10.1021/jo301455n

  日期：2013.3.1

  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.
• Fluorescein Analogue Xanthene-9-Carboxylic Acid: A Transition-Metal-Free CO Releasing Molecule Activated by Green Light
  作者：Lovely Angel Panamparambil Antony、Tomáš Slanina、Peter Šebej、Tomáš Šolomek、Petr Klán

  DOI：10.1021/ol4021089

  日期：2013.9.6

  6-Hydroxy-3-oxo-3H-xanthene-9-carboxylic acid is introduced as the first transition-metal-free carbon monoxide releasing molecule activated by visible light (photoCORM). This water-soluble fluorescein analogue releases carbon monoxide in both water and methanol upon irradiation at 500 nm. When selectively irradiated in the presence of hemoglobin (Hb) under physiological conditions, released CO is quantitatively trapped to form carboxyhemoglobin (COHb). The reaction progress can be accurately monitored by characteristic absorption and emission properties of the reactants and products.