3',6'-dihydroxy-5,10-dimethyl-3H-spiro[anthra[2,3-c]furan-1,9'-xanthen]-3-one | 333956-99-3

• 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',6'-dihydroxy-5,10-dimethyl-3H-spiro[anthra[2,3-c]furan-1,9'-xanthen]-3-one
• CAS: 333956-99-3
• 化学式: C₃₀H₂₀O₅
• 分子量: 460.486
• InChiKey: WOFDFSTYIWTWOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  35.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3',6'-dihydroxy-5,10-dimethyl-3H-spiro[anthra[2,3-c]furan-1,9'-xanthen]-3-one 在 吡啶 、 sodium molybdate 、 sodium hydroxide 作用下， 反应 2.17h， 生成 (6'-Acetyloxy-1,11-dimethyl-7-oxospiro[6,18,19-trioxapentacyclo[9.6.2.02,10.04,8.012,17]nonadeca-2(10),3,8,12,14,16-hexaene-5,9'-xanthene]-3'-yl) acetate
  参考文献：
  名称：

  Rational Design of Fluorescein-Based Fluorescence Probes. Mechanism-Based Design of a Maximum Fluorescence Probe for Singlet Oxygen

  摘要：

  Fluorescein is one of the best available fluorophores for biological applications, but the factors that control its fluorescence properties are not fully established. Thus, we initiated a study aimed at providing a strategy for rational design of functional fluorescence probes bearing fluorescein structure. We have synthesized various kinds of fluorescein derivatives and examined the relationship between their fluorescence properties and the highest occupied molecular orbital (HOMO) levels of their benzoic acid moieties obtained by semiempirical PM3 calculations. It was concluded that the fluorescence properties of fluorescein derivatives are controlled by a photoinduced electron transfer (PET) process from the benzoic acid moiety to the xanthene ring and that the threshold of fluorescence OFF/ON switching lies around -8.9 eV for the HOMO level of the benzoic acid moiety. This information provides the basis for a practical strategy for rational design of functional fluorescence probes to detect certain biomolecules. We used this approach to design and synthesize 9-[2-(3-carboxy-9,10- dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one (DMAX) as a singlet oxygen probe and confirmed that it is the most sensitive probe currently known for O-1(2). This novel fluorescence probe has a 9,10-dimethylanthracene moiety as an extremely fast chemical trap of O-1(2). AS was expected from PM3 calculations, DMAX scarcely fluoresces; while DMAX endoperoxide (DMAX-EP) is strongly fluorescent. Further, DMAX reacts with O-1(2) more rapidly, and its sensitivity is 53-fold higher than that of 9-[2-(3-carboxy-9,10-diphenyl)-anthryl]-6-hydroxy-3H-xanthen-3-ones (DPAX), which are a series of fluorescence probes for singlet oxygen that we recently developed. DMAX should be useful as a fluorescence probe for detecting O-1(2) in a variety of biological systems.

  DOI：

  10.1021/ja0035708
• 作为产物：
  描述：

  9,10-dimethyl-2,3-anthracenedicarboxylic acid 在 甲烷磺酸 、 乙酸酐 作用下， 反应 24.17h， 生成 3',6'-dihydroxy-5,10-dimethyl-3H-spiro[anthra[2,3-c]furan-1,9'-xanthen]-3-one
  参考文献：
  名称：

  Rational Design of Fluorescein-Based Fluorescence Probes. Mechanism-Based Design of a Maximum Fluorescence Probe for Singlet Oxygen

  摘要：

  Fluorescein is one of the best available fluorophores for biological applications, but the factors that control its fluorescence properties are not fully established. Thus, we initiated a study aimed at providing a strategy for rational design of functional fluorescence probes bearing fluorescein structure. We have synthesized various kinds of fluorescein derivatives and examined the relationship between their fluorescence properties and the highest occupied molecular orbital (HOMO) levels of their benzoic acid moieties obtained by semiempirical PM3 calculations. It was concluded that the fluorescence properties of fluorescein derivatives are controlled by a photoinduced electron transfer (PET) process from the benzoic acid moiety to the xanthene ring and that the threshold of fluorescence OFF/ON switching lies around -8.9 eV for the HOMO level of the benzoic acid moiety. This information provides the basis for a practical strategy for rational design of functional fluorescence probes to detect certain biomolecules. We used this approach to design and synthesize 9-[2-(3-carboxy-9,10- dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one (DMAX) as a singlet oxygen probe and confirmed that it is the most sensitive probe currently known for O-1(2). This novel fluorescence probe has a 9,10-dimethylanthracene moiety as an extremely fast chemical trap of O-1(2). AS was expected from PM3 calculations, DMAX scarcely fluoresces; while DMAX endoperoxide (DMAX-EP) is strongly fluorescent. Further, DMAX reacts with O-1(2) more rapidly, and its sensitivity is 53-fold higher than that of 9-[2-(3-carboxy-9,10-diphenyl)-anthryl]-6-hydroxy-3H-xanthen-3-ones (DPAX), which are a series of fluorescence probes for singlet oxygen that we recently developed. DMAX should be useful as a fluorescence probe for detecting O-1(2) in a variety of biological systems.

  DOI：

  10.1021/ja0035708