Tetrahydroquinoline

Tetrahydroquinoline
Names
	IUPAC name 1,2,3,4-Tetrahydroquinoline
	Other names Hydroquinoline
Identifiers
CAS Number	635-46-1;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.010.216
PubChem CID	69460;
UNII	CCR50N1Z9G;
CompTox Dashboard (EPA)	DTXSID8060903 ;
	SMILES C1CC2=CC=CC=C2NC1;
Properties
Chemical formula	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)
	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]

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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". 92: 213–226. doi:10.15227/orgsyn.092.0213. Cite journal requires |journal= (help)
Imaizumi, Taku; Okano, Kentaro; Tokuyama, Hidetoshi (2016). "DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime". 93: 1–13. doi:10.1002/0471264229.os093.01. Cite journal requires |journal= (help)

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[1] 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.

[2] 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.

[3] 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". 92: 213–226. doi:10.15227/orgsyn.092.0213. Cite journal requires |journal= (help)

[4] Imaizumi, Taku; Okano, Kentaro; Tokuyama, Hidetoshi (2016). "DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime". 93: 1–13. doi:10.1002/0471264229.os093.01. Cite journal requires |journal= (help)