Tetrahydroquinoline

Tetrahydroquinoline
Names
Preferred IUPAC name
1,2,3,4-Tetrahydroquinoline
Other names
Hydroquinoline
Identifiers
CAS Number
  • 635-46-1
3D model (JSmol)
  • Interactive image
Beilstein Reference
 116149
ChEBI
  • CHEBI:213323
ChEMBL
  • ChEMBL303611
ChemSpider
  • 62667
ECHA InfoCard 100.010.216 Edit this at Wikidata
EC Number
  • 211-237-6
Gmelin Reference
 27202
PubChem CID
  • 69460
UNII
  • CCR50N1Z9G
CompTox Dashboard (EPA)
  • DTXSID8060903 Edit this at Wikidata
InChI
  • InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2
    Key: LBUJPTNKIBCYBY-UHFFFAOYSA-N
  • 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)
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation markGHS08: Health hazard
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).
Infobox references
Chemical compound

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

  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". Organic Syntheses. 92: 213–226. doi:10.15227/orgsyn.092.0213.
  4. ^ 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.