1159997-92-8

Upstream product

• 1159997-91-7 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline 
• 38925-76-7 N-phenethyl-4-(trifluoromethyl)benzamide 
• 757880-98-1 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 76304-18-2 1-(4′-trifluoromethylphenyl)isoquinoline 
• 64-04-0 phenethylamine 

Downstream Products

• 1159996-53-8 (R)-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone 
• 1159997-39-3 (R)-N-cyclopropyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159996-98-1 (1R)-2-(tricyclo[3.3.1.1(3,7)]dec-1-ylcarbonyl)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1159997-32-6 (R)-N-(2-(trifluoromethyl)phenyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159997-27-9 (R)-1-(4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1589602-03-8 (R)-N-(2-fluorophenyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159997-55-3 (R)-ethyl-4-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)benzoate 
• 1159997-31-5 (R)-N-(4-cyanophenyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159996-39-0 (R)-N-(pyridin-3-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1589602-04-9 N-isopropyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159997-65-5 (R)-1-(4-(trifluoromethyl)phenyl)-N-((R)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159996-43-6 (R)-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1159997-56-4 (R)-4-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)benzoic acid 
• 1159996-55-0 (R)-N-(pyrimidin-5-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroiso-quinoline-2(1H)-carboxamide 

Relevant academic research and scientific papers

Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

A through halogen bond activation isoquinoline asymmetric hydrogenation method

A through halogen bond activation isoquinoline asymmetric hydrogenation method, the catalyzing system is [...] complex, the activator is a halide. The reaction can be carried out under the following conditions, temperature: 25 - 100 °C; solvent: tetrahydr

Asymmetric Hydrogenation of Isoquinolines and Pyridines Using Hydrogen Halide Generated in Situ as Activator

By employing halogenide trichloroisocyanuric acid as a traceless activation reagent, a general iridium-catalyzed asymmetric hydrogenation of isoquinolines and pyridines is developed with up to 99% ee. This method avoids tedious steps of installation and removal of the activating groups. The mechanism studies indicated that hydrogen halide generated in situ acted as an activator of isoquinolines and pyridines.

One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines

A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.

Enantioselective hydrogenation of cyclic imines catalysed by Noyori-Ikariya half-sandwich complexes and their analogues

A method for enantioselective hydrogenation of cyclic imines with gaseous hydrogen has been developed. Easily accessible Noyori-Ikariya Ru(ii) and Rh(iii) complexes can be used directly without an inert atmosphere. Substrate activation has been achieved by trifluoroacetic acid. A new hydroxyl-functionalized complex is reported, showing high activity in transfer hydrogenation.

Optimization of potency and pharmacokinetic properties of tetrahydroisoquinoline transient receptor potential melastatin 8 (TRPM8) antagonists

Transient receptor potential melastatin 8 (TRPM8) is a nonselective cation channel expressed in a subpopulation of sensory neurons in the peripheral nervous system. TRPM8 is the predominant mammalian cold temperature thermosensor and is activated by cold temperatures ranging from 8 to 25 °C and cooling compounds such as menthol or icilin. TRPM8 antagonists are being pursued as potential therapeutics for treatment of pain and bladder disorders. This manuscript outlines new developments in the SAR of a lead series of 1,2,3,4-tetrahydroisoquinoline derivatives with emphasis on strategies to improve pharmacokinetic properties and potency. Selected compounds were profiled in two TRPM8 target-specific in vivo coverage models in rats (the icilin-induced wet dog shake model and the cold pressor test). Compound 45 demonstrated robust efficacy in both pharmacodynamic models with ED90 values 3 mg/kg.

The role of the aromatic ligand in the asymmetric transfer hydrogenation of the CN bond on Noyori's chiral Ru catalysts

Only four types of dimeric precursors [RuCl2(η6-arene)]2 for the synthesis of Noyori's half sandwich diamine catalysts [RuCl(TsDPEN)(η6-arene)] are commercially available, yet so far no study has tried to system

Asymmetric transfer hydrogenation of 1-phenyl dihydroisoquinolines using Ru(II) diamine catalysts

A new [Ru(II)(η6-p-cymene)(1R,2R)-N-((1S,2S)-borneol-10- sulfonyl)-1,2-diphenylethylenediamine] catalyst for the asymmetric transfer hydrogenation of both 1-alkyl and 1-aryl dihydroisoquinolines has been isolated. For the first time in this type of reaction, the catalyst employs an N-alkylsulfonyl group instead of N-arylsulfonyl.