57680-86-1

Basic information

• Product Name: Isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-, (1S)-
• CAS NO: 57680-86-1
• Molecular Formula: C16H17N
• Molecular Weight: 223.318
• Mol File: 57680-86-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-, (1S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-, (1S)-(57680-86-1)
• EPA Substance Registry System: Isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-, (1S)-(57680-86-1)

Safety Data

• Hazardous Substances Data: 57680-86-1(Hazardous Substances Data)

Upstream product

• 19716-56-4 1-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 6907-59-1 1-benzylisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 350678-46-5 (S)-1-Benzyl-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 350678-38-5 N-(2-Benzenesulfinyl-ethyl)-N-((S)-1,2-diphenyl-ethyl)-formamide 
• 350678-34-1 N-((S)-1,2-Diphenyl-ethyl)-N-(2-phenylsulfanyl-ethyl)-formamide 
• 350678-30-7 ((S)-1,2-Diphenyl-ethyl)-(2-phenylsulfanyl-ethyl)-amine 
• 3082-58-4 (S)-1,2-diphenylethyl amine 
• 25611-78-3 (R,S)-1,2-diphenylethylamine 
• 6921-34-2 benzylmagnesium chloride 
• 84010-65-1 [1-(3,4-Dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 350678-51-2 (S)-1-Benzyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 102922-33-8 (R)-1-Benzyl-2-((S)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline 
• 90482-02-3 (S)-valinol-tert-butyl ether formamidine of 1,2,3,4 tetrahydro-isoquinoline 

Downstream Products

• 131-10-2 (-)-berbine 

Relevant articles and documents

Asymmetric Alkylation of α-Amino Carbanions. An Enantioselective Synthesis of (S)-1-Alkyl-1,2,3,4-tetrahydroisoquinolines

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Enhancing effects of salt formation on catalytic activity and enantioselectivity for asymmetric hydrogenation of isoquinolinium salts by dinuclear halide-bridged iridium complexes bearing chiral diphosphine ligands

Asymmetric hydrogenation of 1- and 3-substituted and 1,3-disubstituted isoquinolinium chlorides using triply halide-bridged dinuclear iridium complexes [{Ir(H)(diphosphine)} 2(μ -Cl)3]Cl has been achieved by the strategy of HCl salt formation of isoquinolines to afford the corresponding chiral 1,2,3,4-tetrahydroisoquinolines (THIQs) in high yields and with excellent enantioselectivities after simple basic workup. The effects of salt formation have been investigated by time-course experiments, which revealed that the generation of isoquinolinium chlorides clearly prevented formation of the catalytically inactive dinuclear trihydride complex, which was readily generated in the catalytic reduction of salt-free isoquinoline substrates. Based on mechanistic investigations, including by 1H and 31P{1H} NMR studies and the isolation and characterization of several intermediates, the function of the chloride anion of the isoquinolinium chlorides has been elucidated, allowing us to propose a new outer-sphere mechanism involving coordination of the chloride anion of the substrates to an iridium dihydride species along with a hydrogen bond between the chloride ligand and the N-H proton of the substrate salt.

Determination of ring conformation in 1-benzyl-1,2,3,4- tetrahydroisoquinolines and a new synthesis of the chiral compounds

The conformation of the piperideine ring in 1-benzyl-1,2,3,4- tetrahydroisoquinolines was determined as 2H3 form with a pseudoaxial position of the 1-benzyl group by circular dichroism (CD) spectral comparison with 1-methyl-1,2,3,4-tetrahydroisoquinolines. The chiral center at C-1 of 1,2,3,4-tetrahydroisoquinoline (TIQ) was constructed in an unambiguous manner by applying a new method of TIQ synthesis utilizing the Pummerer reaction as a key step. Enantiomerically pure (R)- and (S)-1-methyl- and 1- benzyltetrahydroisoquinolines (1) were prepared starting from readily available chiral amines (2) in good overall yields.