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Details

Stereochemistry ACHIRAL
Molecular Formula C9H11N
Molecular Weight 133.1903
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,2,3,4-TETRAHYDROQUINOLINE

SMILES

C1CNC2=CC=CC=C2C1

InChI

InChIKey=LBUJPTNKIBCYBY-UHFFFAOYSA-N
InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2

HIDE SMILES / InChI

Molecular Formula C9H11N
Molecular Weight 133.1903
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
(3S)-2-Benzyl-3-carb-oxy-1,2,3,4-tetra-hydro-isoquinolinium chloride monohydrate.
2010-12-24
Functional importance of tyrosine 294 and the catalytic selectivity for the bis-Fe(IV) state of MauG revealed by replacement of this axial heme ligand with histidine .
2010-11-16
Preparation of half-metallocenes of thiophene-fused and tetrahydroquinoline-linked cyclopentadienyl ligands for ethylene/α-olefin copolymerization.
2010-11-07
InCl3-catalyzed allylic Friedel-Crafts reactions toward the stereocontrolled synthesis of 1,2,3,4-tetrahydroquinolines.
2010-11-05
Synthesis, testing and structure-activity studies on a library of 5-HT₄ ligands.
2010-11
Comparison of the activity of non-steroidal ecdysone agonists between dipteran and lepidopteran insects, using cell-based EcR reporter assays.
2010-11
Enantioselective organocatalytic C-H bond functionalization via tandem 1,5-hydride transfer/ring closure: asymmetric synthesis of tetrahydroquinolines.
2010-09-01
Quinoline-based compounds as modulators of HIV transcription through NF-kappaB and Sp1 inhibition.
2010-09
5,8-Dimeth-oxy-2-phenyl-1,4-dihydro-quinoline-3-carbonitrile.
2010-08-18
A small-molecule oxocarbazate inhibitor of human cathepsin L blocks severe acute respiratory syndrome and ebola pseudotype virus infection into human embryonic kidney 293T cells.
2010-08
Quinaphos and Dihydro-Quinaphos phosphine-phosphoramidite ligands for asymmetric hydrogenation.
2010-07-05
Palladium-catalyzed ring-expansion reaction of indoles with alkynes: from indoles to tetrahydroquinoline derivatives under mild reaction conditions.
2010-06-01
Asymmetric three-component inverse electron-demand aza-Diels-Alder reaction: efficient synthesis of ring-fused tetrahydroquinolines.
2010-05-17
Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.
2010-05-07
Diverse effects on mitochondrial and nuclear functions elicited by drugs and genetic knockdowns in bloodstream stage Trypanosoma brucei.
2010-05-04
Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents.
2010-05
Assessment of species specificity of moulting accelerating compounds in Lepidoptera: comparison of activity between Bombyx mori and Spodoptera littoralis by in vitro reporter and in vivo toxicity assays.
2010-05
Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles.
2010-03-31
Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.
2010-03-05
Novel tetrahydrochinoline derived CETP inhibitors.
2010-03-01
Zn(OTf)2-catalyzed reactions of ethenetricarboxylates with 2-aminobenzaldehydes leading to tetrahydroquinoline derivatives.
2010-02-19
Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.
2010-02-05
Easy access to isoquinolines and tetrahydroquinolines from ketoximes and alkynes via rhodium-catalyzed C-H bond activation.
2009-12-18
Tetrahydroquinoline derivatives as CRTH2 antagonists.
2009-12-15
N,1-Bis(4-chloro-2-methyl-benz-yl)-3-methyl-2-oxo-1,2,3,4-tetra-hydro-quinoline-3-carboxamide.
2009-11-14
Tetrahydroquinoline sulfonamides as vasopressin 1b receptor antagonists.
2009-11-01
Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety.
2009-10
Substituted tetrahydroquinolines as potent allosteric inhibitors of reverse transcriptase and its key mutants.
2009-09-01
Gold-catalyzed intramolecular allylic amination of 2-tosylaminophenylprop-1-en-3-ols. A concise synthesis of (+/-)-angustureine.
2009-08-21
Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors.
2009-08-01
Improved asymmetric synthesis of 3,4-dihydro-2-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-alpha-(trifluoromethyl)-1(2H)-quinolineethanol, a potent cholesteryl ester transfer protein inhibitor.
2009-07-02
Synthesis and biotransformation of tetrahydroquinoline by Mortierella isabelina.
2009-06-17
Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform.
2009-05-01
Self-assembly of hydrogensquarates: crystal structures and properties.
2009-04-02
Substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes as beta3-adrenergic receptor agonists: design, synthesis, biological evaluation and pharmacophore modeling.
2009-01-15
Lewis acid or Brønsted acid catalyzed reactions of vinylidene cyclopropanes with activated carbon-nitrogen, nitrogen-nitrogen, and iodine-nitrogen double-bond-containing compounds.
2009
QSAR study on tetrahydroquinoline analogues as plasmodium protein farnesyltransferase inhibitors: a comparison of rationales of malarial and mammalian enzyme inhibitory activities for selectivity.
2008-12
Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives.
2008-11-20
Bis(1,2,3,4-tetra-hydro-quinolin-6-yl)methane.
2008-08-13
Ruthenium-catalyzed enantioselective carbon-carbon bond forming reaction via allenylidene-ene process: synthetic approach to chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives.
2008-08-13
Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries.
2008-08
Synthesis and characterization of 5,6,7,8-tetrahydroquinoline C5a receptor antagonists.
2008-04-15
Suzuki-Miyaura approach to JNJ-26076713, an orally active tetrahydroquinoline-containing alphaVbeta3/alphaVbeta5 integrin antagonist. enantioselective synthesis and stereochemical studies.
2008-03-21
Strictosidine synthase: mechanism of a Pictet-Spengler catalyzing enzyme.
2008-01-16
Selective androgen receptor modulators in preclinical and clinical development.
2008
Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives.
2008
Development of pinene-derived N,P ligands and their utility in catalytic asymmetric hydrogenation.
2007-12-21
Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells.
2007-11
Heteroarotinoids with anti-cancer activity against ovarian cancer cells.
2007-10-24
Moexipril and left ventricular hypertrophy.
2007
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:55:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:55:17 GMT 2025
Record UNII
CCR50N1Z9G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,2,3,4-TETRAHYDROQUINOLINE
Systematic Name English
KUSOL
Preferred Name English
NSC-15311
Code English
1,2,3,4-HYDROQUINOLINE
Common Name English
QUINOLINE, 1,2,3,4-TETRAHYDRO-
Systematic Name English
Code System Code Type Description
SMS_ID
300000052881
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
CHEBI
213323
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
FDA UNII
CCR50N1Z9G
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
CAS
635-46-1
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
PUBCHEM
69460
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
211-237-6
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
WIKIPEDIA
Tetrahydroquinoline
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
MESH
C542964
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
NSC
15311
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID8060903
Created by admin on Mon Mar 31 18:55:17 GMT 2025 , Edited by admin on Mon Mar 31 18:55:17 GMT 2025
PRIMARY