Tetrahydroquinoline
 | |
| Names | |
|---|---|
| Preferred IUPAC name 1,2,3,4-Tetrahydroquinoline | |
| Other names Hydroquinoline | |
| Identifiers | |
3D model (JSmol) | |
| 116149 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.010.216 |
| EC Number |
|
| 27202 | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
| |
| |
| 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 labelling: | |
  | |
| Danger | |
| H315, H319, H335, H350 | |
| P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
| Related compounds | |
Related compounds | Quinoline, Tetralin, Chromane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil.
Use
[edit]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
[edit]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
[edit]- ^ 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. Vol. 93. pp. 1–13. doi:10.1002/0471264229.os093.01. ISBN 9780471264224. S2CID 251970071.