9,10-dimethyl-2,3-anthracenedicarboxylic acid | 333957-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dimethyl-2,3-anthracenedicarboxylic acid
• 英文别名: 9,10-dimethylanthracene-2,3-dicarboxylic acid
• CAS: 333957-04-3
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: LZBFVTFUGDTGAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,3-dibromo-9,10-dimethylanthracene 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 生成 9,10-dimethyl-2,3-anthracenedicarboxylic acid
  参考文献：
  名称：

  REAGENT FOR DETERMINING SINGLET OXYGEN

  摘要：

  公开号：

  EP1314730B1

文献信息

• Agent for measurement of singlet oxygen
  申请人：Nagano Tetsuo

  公开号：US20050123478A1

  公开（公告）日：2005-06-09

  Compounds useful as agents for measurement of singlet oxygen, which are represented by the following general formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 independently represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, or a C 1-6 alkoxyl group, R 7 and R 8 independently represent a C 1-4 alkyl group, and R 9 represents a hydrogen atom, a C 1-12 alkanoyl group, or acetoxymethyl group, or salts thereof.

  以下为可用作单线态氧测量试剂的化合物，其通式如下（I）： 其中，R1、R2、R3、R4、R5和R6独立地表示氢原子、卤素原子、C1-6烷基或C1-6烷氧基基团，R7和R8独立地表示C1-4烷基，R9表示氢原子、C1-12烷酰基或乙酰甲基基团，或其盐。
• Reagent for determining singlet oxygen
  申请人：——

  公开号：US20040043498A1

  公开（公告）日：2004-03-04

  Compounds useful as agents for measurement of singlet oxygen, which are represented by the following general formula (I): 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 independently represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, or a C 1-6 alkoxyl group, R 7 and R 8 independently represent a C 1-4 alkyl group, and R 9 represents a hydrogen atom, a C 1-12 alkanoyl group, or acetoxymethyl group, or salts thereof.

  以下是可用作单线态氧测量剂的化合物，其通式表示为(I)：1其中R1、R2、R3、R4、R5和R6分别独立地表示氢原子、卤素原子、C1-6烷基或C1-6烷氧基；R7和R8独立地表示C1-4烷基；R9表示氢原子、C1-12烷酰基或乙酰氧甲基基团或其盐。
• REAGENT FOR DETERMINING SINGLET OXYGEN
  申请人：DAIICHI PURE CHEMICALS CO., LTD.

  公开号：EP1314730B1

  公开（公告）日：2007-01-10
• Rational Design of Fluorescein-Based Fluorescence Probes. Mechanism-Based Design of a Maximum Fluorescence Probe for Singlet Oxygen
  作者：Kumi Tanaka、Tetsuo Miura、Naoki Umezawa、Yasuteru Urano、Kazuya Kikuchi、Tsunehiko Higuchi、Tetsuo Nagano

  DOI：10.1021/ja0035708

  日期：2001.3.1

  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.