tetrahydroquinoline
{{Chembox
| ImageFile = Tetrahydroquinoline structure.svg
| ImageSize = 166 px
| ImageAlt =
| PIN = 1,2,3,4-Tetrahydroquinoline
| OtherNames = Hydroquinoline
|Section1={{Chembox Identifiers
| CASNo = 635-46-1
| PubChem = 69460
| ChemSpiderID = 62667
| EC_number = 211-237-6
| ChEBI = 213323
| ChEMBL = 303611
| UNII = CCR50N1Z9G
| Beilstein = 116149
| Gmelin = 27202
| StdInChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2
| StdInChIKey = LBUJPTNKIBCYBY-UHFFFAOYSA-N
| SMILES = C1CC2=CC=CC=C2NC1}}
|Section2={{Chembox Properties
| C=9|H=11|N=1
| MolarMass =
| Appearance = Colorless oily liquid
| Density = 1.0599 g/cm3
| MeltingPtC = 20
| BoilingPtC = 251
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|315|319|335|350}}
| PPhrases = {{P-phrases|201|202|261|264|271|280|281|302+352|304+340|305+351+338|308+313|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
|Section8={{Chembox Related
|OtherCompounds = Quinoline, Tetralin, Chromane
}}
}}
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.{{cite journal|doi=10.1021/cr100307m|pmid=21830756|title=Advances in the Chemistry of Tetrahydroquinolines|year=2011|last1=Sridharan|first1=Vellaisamy|last2=Suryavanshi|first2=Padmakar A.|last3=Menéndez|first3=J. Carlos|journal=Chemical Reviews|volume=111|issue=11|pages=7157–7259}} Oxamniquine, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines.{{cite journal|title=Recent Progress in the Synthesis of 1,2,3,4-Tetrahydroquinolines |last1=Katritzky |first1=Alan R.|last2=Rachwal |first2=Stanislaw |last3=Rachwal |first3=Bogumila|journal=Tetrahedron|year=1996|volume=52|issue=48 |pages=15031–15070|doi=10.1016/S0040-4020(96)00911-8}} 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.
{{cite journal|title=Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst|author1= Chen, Fei|author2= Ding, Zi-Yuan|author3=He, Yan-Mei |author4= Fan, Qing-Hua|journal= Organic Syntheses|year=2015|volume=92|pages=213–226|doi=10.15227/orgsyn.092.0213|doi-access=free}} It can also be prepared from 1-indanone (benzocyclopentanone).{{cite book|chapter=DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime| first1=Taku|last1=Imaizumi|first2=Kentaro|last2=Okano|first3=Hidetoshi|last3=Tokuyama| title=Organic Syntheses|year=2016|volume=93|pages=1–13|doi=10.1002/0471264229.os093.01| isbn=9780471264224| s2cid=251970071}}