Chemistry:Tetrahydroquinoline
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| Names | |
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| Preferred IUPAC name
1,2,3,4-Tetrahydroquinoline | |
| Other names
Hydroquinoline
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| Identifiers | |
3D model (JSmol)
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| 116149 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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| 27202 | |
PubChem CID
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| UNII | |
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| Properties | |
| C9H11N | |
| Molar mass | 133.194 g·mol−1 |
| Appearance | Colorless oily liquid |
| Density | 1.0599 g/cm3 |
| Melting point | 20 °C (68 °F; 293 K) |
| Boiling point | 251 °C (484 °F; 524 K) |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Danger |
| H315, H319, H335, H350 | |
| P201, P202, P261, P264, P271, P280, P281, P302+352, P304+340, P305+351+338, P308+313, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
| Related compounds | |
Related compounds
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Quinoline, Tetralin, Chromane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil.
Use
Substituted derivatives of tetrahydroquinoline are common in medicinal chemistry.[1] Oxamniquine, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines.[2] Typically tetrahydroquinoline derivatives are prepared by hydrogenation of the corresponding quinoline using heterogeneous catalysts.
Synthesis
Tetrahydroquinolines are produced by hydrogenation of quinolines. Because the hydrogenation is reversible, tetrahydroquinoline has been often examined as a hydrogen-donor solvent in coal liquifaction.
Using homogeneous catalysts, asymmetric hydrogenation has been demonstrated.[3] It can also be prepared from 1-indanone (benzocyclopentanone).[4]
References
- ↑ Sridharan, Vellaisamy; Suryavanshi, Padmakar A.; Menéndez, J. Carlos (2011). "Advances in the Chemistry of Tetrahydroquinolines". Chemical Reviews 111 (11): 7157–7259. doi:10.1021/cr100307m. PMID 21830756.
- ↑ Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila (1996). "Recent Progress in the Synthesis of 1,2,3,4-Tetrahydroquinolines". Tetrahedron 52 (48): 15031–15070. doi:10.1016/S0040-4020(96)00911-8.
- ↑ Chen, Fei; Ding, Zi-Yuan; He, Yan-Mei; Fan, Qing-Hua (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Organic Syntheses 92: 213–226. doi:10.15227/orgsyn.092.0213.
- ↑ Imaizumi, Taku; Okano, Kentaro; Tokuyama, Hidetoshi (2016). "DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime". Organic Syntheses. 93. pp. 1–13. doi:10.1002/0471264229.os093.01. ISBN 9780471264224.
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