1312162-96-1

Basic information

• Product Name: (R)-2-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydroquinoline
• CAS NO: 1312162-96-1
• Molecular Weight: 277.289
• Mol File: 1312162-96-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-2-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydroquinoline(1312162-96-1)
• EPA Substance Registry System: (R)-2-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydroquinoline(1312162-96-1)

Safety Data

• Hazardous Substances Data: 1312162-96-1(Hazardous Substances Data)

Upstream product

• 396-84-9 2-(3-(trifluoromethyl)phenyl)quinoline 
• 5344-90-1 2-Aminobenzyl alcohol 
• 349-76-8 3'-(trifluoromethyl)acetophenone 

Relevant articles and documents

Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic Ruthenium catalysts: Scope, mechanism, and origin of enantioselectivity

Asymmetric hydrogenation of quinolines catalyzed by chiral cationic η6-arene-N-tosylethylenediamine-Ru(II) complexes have been investigated. A wide range of quinoline derivatives, including 2-alkylquinolines, 2-arylquinolines, and 2-functionalized and 2,3-disubstituted quinoline derivatives, were efficiently hydrogenated to give 1,2,3,4-tetrahydroquinolines with up to >99% ee and full conversions. This catalytic protocol is applicable to the gram-scale synthesis of some biologically active tetrahydroquinolines, such as (-)-angustureine, and 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, a key intermediate for the preparation of the antibacterial agent (S)-flumequine. The catalytic pathway of this reaction has been investigated in detail using a combination of stoichiometric reaction, intermediate characterization, and isotope labeling patterns. The evidence obtained from these experiments revealed that quinoline is reduced via an ionic and cascade reaction pathway, including 1,4-hydride addition, isomerization, and 1,2-hydride addition, and hydrogen addition undergoes a stepwise H+/H- transfer process outside the coordination sphere rather than a concerted mechanism. In addition, DFT calculations indicate that the enantioselectivity originates from the CH/π attraction between the η6-arene ligand in the Ru-complex and the fused phenyl ring of dihydroquinoline via a 10-membered ring transition state with the participation of TfO- anion.