4-Quinolone
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| Names | |
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| Preferred IUPAC name
Quinolin-4(1H)-one | |
| Other names
1H-Quinolin-4-one
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ECHA InfoCard | 100.009.336 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H7NO | |
| Molar mass | 145.161 g·mol−1 |
| Melting point | 208–210 °C (406–410 °F; 481–483 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-Quinolone is an organic compound derived from quinoline. It and 2-quinolone are the two most important parent (meaning simplified) quinolones. 4-Quinolone exists in equilibrium with a minor tautomer, 4-hydroxyquinoline (CAS#611-36-9). Aside from pedagogical interest, 4-quinolone is of little intrinsic value but its derivatives, the 4-quinolone antibiotics, represent a large class of important drugs.[1]
Synthesis
[edit]The chemical synthesis of quinolones often involves ring-closing reactions.[2] Such reactions often install a hydroxyl group (an –OH functional group) on the carbon across from the ring nitrogen (i.e., the C-4 positions). An example of such a synthesis is the Camps cyclization, which, depending on starting materials and reaction conditions, can give both 2-hydroxyquinolines (B) and 4-hydroxyquinolines (A) as shown. The hydroxyquinolines tautomerize to the quinolones.
