Tetrahydroquinoline

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Tetrahydroquinoline
Tetrahydroquinoline structure.svg
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 Edit this at Wikidata
EC Number
  • 211-237-6
27202
UNII
  • 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
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:
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).

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]

  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.