89160-45-2

Usage

InChI:InChI=1/C15H15N/c1-2-6-12(7-3-1)15-11-16-10-13-8-4-5-9-14(13)15/h1-9,15-16H,10-11H2/t15-/m1/s1

Upstream product

• 75626-12-9 4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 100-52-7 benzaldehyde 
• 88393-58-2 (R)-N-benzyl-2-hydroxy-2-phenylacetamide 
• 51019-43-3 (R)-(-)-O-acetylmandelic acid 
• 1408381-76-9 (4R)-4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 100-46-9 benzylamine 
• 81384-43-2 2-(benzylamino)-2-oxo-1-phenylethyl acetate 
• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 
• 1492030-89-3 dibenzyl[(2R)-2-iodo-2-phenylethyl]amine 
• 197142-90-8 (S)-2-(N,N-dibenzylamino)-2-phenyl-1-ethanol 
• 51096-49-2 2-benzylamino-1-phenyl-ethanol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 928209-91-0 1-[2-(5,9-diethyl-5,9-dihydro-6,8-dioxa-benzocyclohepten-7-yl)-phenyl]-2-nitro-ethanol 
• 928209-95-4 5,9-diethyl-7-[2-(2-nitro-vinyl)-phenyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene 

Relevant academic research and scientific papers

Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri

A new chemoenzymatic approach to the synthesis of chiral 4-aryl-1,4-dihydro-2H-isoquinolines via the enzymatic resolution of 2-acetyl-4-phenyl-1,4-dihydro-2H-isoquinolin-3-one

A new chemoenzymatic method is proposed for the synthesis of enantiomerically pure 4-phenyl-1,4-dihydro-2H-isoquinolines based on the enzymatic kinetic resolution of 2-acetyl-4-phenyl-1,4-dihydro-2H-isoquinolin-3- one. For the enzymatic resolution of the racemic substrate, readily available 'home made' animal liver acetone powders (LAPs) were used. Excellent enantioselectivity, exceeding 500, was achieved in a short reaction time upon application of turkey liver acetone powder as the biocatalyst. Reduction of obtained product led to the formation of amine (R)-1, which is hardly available using standard procedures. These results show that N-acetyl lactams are a new type of substrate for enzymatic biotransformations.

Highly diastereoselective conjugate addition of aryllithium to chiral β-nitrostyrene derivative: An application to the asymmetric synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline

Highly diastereoselective conjugate addition of aryllithium to β-nitrostyrene derivative, having chiral acetal moiety derived from (S,S)-1,2-bis(1-hydroxypropyl)benzene, was achieved. The adduct was transformed to 4-aryl-1,2,3,4-tetrahydroisoquinoline in

Synthesis and enantioselectivity of optically active 1- and 3-substituted 4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols and related compounds as norepinephrine potentiators

Optically active 1,2-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4- ols (1R,4R-3a and 1S,4S-3b, 1S,4R-4a, and 1R,4S-4b) and 2-methyl-4-phenyl- 1,2,3,4-tetrahydroisoquinolines (4S-5a and 4R-5b) were prepared in order to examine the effects of the 1-, 3-, and 4-substituents of 2-methyl-4-phenyl- 1,2,3,4-tetrahydroisoquinolin-4-ol (PI-OH) (1) on the enantioselectivity for norepinephrine (NE) potentiating activity. The conformations and absolute configurations of 3-5 were determined from their 1H-NMR and circular dichroism (CD) spectra and by single-crystal X-ray diffractometric analysis. The NE potentiating activity of the optically active 3-5 and previously prepared 3-methyl derivatives (3R,4R-6a and 3S,4S-6b) of PI-OH were tested. The results show that compounds 3, 4, and 6 had high enantioselectivity for NE potentiation: the 4R series of the enantiomers exhibited activity but not the 4S-enantiomers. The activity of the 4-desoxy compound 5 also resided exclusively in the 4S-enantiomer. These findings suggest the presence of a specific receptor for NE uptake, and the enantiomers 3a, 4a, 5a, and 6a may be antagonistic at this NE uptake receptor.