1240163-16-9

Upstream product

• 1219687-55-4 2-benzyl 3-methyl (1R,3S)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate 
• 501-53-1 benzyl chloroformate 
• 1276098-04-4 (1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 

Downstream Products

• 1240163-18-1 (1R,3S)-benzyl 3-((R)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1240163-19-2 (1R,3S)-benzyl 3-((S)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1373440-40-4 benzyl (1R,3S)-3-carbamoyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 1373440-41-5 benzyl (1R,3S)-3-carbamothioyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 1373440-42-6 benzyl (1R,3S)-6,7-dimethoxy-1-phenyl-3-(4-phenyl-1,3-thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 1373440-43-7 benzyl (1R,3S)-3-(4-tert-butyl-1,3-thiazol-2-yl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 1352834-57-1 2-((1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-4-phenylthiazole 
• 1373440-46-0 4-tert-butyl-2-((1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)thiazole 
• 1392284-41-1 (1R,3S)-benzyl 3-(2,6-diisopropylphenylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1392429-20-7 C₄₃H₅₈N₄O₃ 
• 1219687-56-5 [(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol 
• 1219687-55-4 2-benzyl 3-methyl (1R,3S)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate 

Relevant academic research and scientific papers

Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 μM for the cis-dia-stereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4.

Microwave-assisted synthesis of guanidine organocatalysts bearing a tetrahydroisoquinoline framework and their evaluation in Michael addition reactions

The simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and β-keto esters with nitro-olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave-assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported. The chiral products were obtained with quantitative chemical efficiency (up to 99 % yield) and excellent enantioselectivity (up to 97 % ee). Copyright

Synthesis of tetrahydroisoquinoline (TIQ)-oxazoline ligands and their application in enantioselective Henry reactions

A novel family of eleven new tetrahydroisoquinoline (TIQ)-oxazoline intermediates and five corresponding copper(II) catalysts has been developed and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide β-hydroxy nitroalkanes in high conversion (>99%). This paper describes the synthesis of the TIQ compounds from L-dihydroxyphenylalanine (L-DOPA) as the starting material. The chiral ligands were complexed in situ with various transition metals such as Cu, Sc, Co, Zn, Ni and Mn and tested as a chiral catalyst for the Henry reaction. The reaction was optimized in terms of the metal, counter ion, solvent, temperature and over a range of substrates. The corresponding catalyst with copper(II) acetate and 2-propanol as the solvent provides the best enantioselectivities (up to 77% ee) of the corresponding nitroalcohol for 4-chlorobenzaldehyde.