26386-86-7 Usage
Description
3-Hydroxyquinolin-2-one, also known as 3-hydroxy-2-quinolinone or 2-hydroxyquinolin-3(2H)one, is a chemical compound belonging to the quinolinone class of organic compounds. It is a derivative of quinoline with a hydroxy group at the 3-position. 3-Hydroxyquinolin-2-one exhibits a range of biological and pharmacological activities, such as antioxidant, anticancer, and antimicrobial properties. Additionally, it has been studied for its potential as a chelating agent for metal ions and as a precursor in the synthesis of heterocyclic compounds. 3-Hydroxyquinolin-2-one holds significant importance in medicinal chemistry and drug discovery due to its diverse applications.
Uses
Used in Pharmaceutical Industry:
3-Hydroxyquinolin-2-one is used as a pharmaceutical agent for its antioxidant properties, which can help protect cells from oxidative damage and contribute to the prevention of various diseases.
3-Hydroxyquinolin-2-one is used as an anticancer agent, targeting various types of cancer cells and potentially enhancing the effectiveness of conventional chemotherapy treatments.
Used in Antimicrobial Applications:
3-Hydroxyquinolin-2-one is used as an antimicrobial agent, exhibiting activity against a range of microorganisms, including bacteria and fungi, making it a potential candidate for the development of new antimicrobial drugs.
Used in Chelating Agent Applications:
3-Hydroxyquinolin-2-one is used as a chelating agent for metal ions, which can be useful in various industrial processes, such as water treatment and metal recovery, as well as in the development of new materials with specific properties.
Used in Synthesis of Heterocyclic Compounds:
3-Hydroxyquinolin-2-one is used as a precursor in the synthesis of heterocyclic compounds, which are important building blocks in the creation of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Check Digit Verification of cas no
The CAS Registry Mumber 26386-86-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,3,8 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 26386-86:
(7*2)+(6*6)+(5*3)+(4*8)+(3*6)+(2*8)+(1*6)=137
137 % 10 = 7
So 26386-86-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H7NO2/c11-8-5-6-3-1-2-4-7(6)10-9(8)12/h1-5,11H,(H,10,12)
26386-86-7Relevant articles and documents
White,Dimsdale
, p. 1285 (1969)
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Huntress,Bornstein
, p. 745 (1949)
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Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis
Zheng, Jian,Swords, Wesley B.,Jung, Hoimin,Skubi, Kazimer L.,Kidd, Jesse B.,Meyer, Gerald J.,Baik, Mu-Hyun,Yoon, Tehshik P.
supporting information, p. 13625 - 13634 (2019/08/26)
Enantioselective catalysis of excited-state photoreactions remains a substantial challenge in synthetic chemistry, and intermolecular photoreactions have proven especially difficult to conduct in a stereocontrolled fashion. Herein, we report a highly enantioselective intermolecular [2 + 2] cycloaddition of 3-alkoxyquinolones catalyzed by a chiral hydrogen-bonding iridium photosensitizer. Enantioselectivities as high as 99% ee were measured in reactions with a range of maleimides and other electron-deficient alkene reaction partners. An array of kinetic, spectroscopic, and computational studies supports a mechanism in which the photocatalyst and quinolone form a hydrogen-bonded complex to control selectivity, yet upon photoexcitation of this complex, energy transfer sensitization of maleimide is preferred. The sensitized maleimide then reacts with the hydrogen-bonded quinolone-photocatalyst complex to afford a highly enantioenriched cycloadduct. This finding contradicts a long-standing tenet of enantioselective photochemistry that held that stereoselective photoreactions require strong preassociation to the sensitized substrate in order to overcome the short lifetimes of electronically excited organic molecules. This system therefore suggests that a broader range of alternate design strategies for asymmetric photocatalysis might be possible.
Enantioselective, intermolecular [2+2] photocycloaddition reactions of 3-acetoxyquinolone: Total synthesis of (-)-pinolinone
Mayr, Florian,Wiegand, Christian,Bach, Thorsten
supporting information, p. 3353 - 3355 (2014/03/21)
The natural product (-)-pinolinone was synthesised via a concise route (six steps, 17% overall yield) from 3-acetoxyquinolone, employing an enantioselective intermolecular [2+2] photocycloaddition as the key step. The Royal Society of Chemistry 2014.
