153218-97-4

Upstream product

• 290347-00-1 (4S*)-N-[(R)-2-hydroxy-1-phenylethyl]-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 100-52-7 benzaldehyde 
• 51096-49-2 2-benzylamino-1-phenyl-ethanol 
• 290347-03-4 (4S*)-N-[(R)-2-hydroxy-1-phenylethyl]-4-phenyl-1,4-dihydroisoquinolin-3-one 
• 290346-99-5 N-[(R)-2-hydroxy-1-phenylethyl]-4-phenyl-1,4-dihydroisoquinolin-3-one 
• 5911-60-4 4-phenylisochroman-3-one 
• 675872-31-8 1-[(R)-2-nitro-1-phenylethyl]-2-trityloxymethylbenzene 
• 675872-80-7 {2-[(R)-2-nitro-1-phenylethyl]phenyl}methanol 
• 132814-55-2 (((2-bromobenzyl)oxy)methanetriyl)tribenzene 
• 5153-67-3 nitrostyrene 
• 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 
• 928209-86-3 7-(2-bromo-phenyl)-5,9-diethyl-5,9-dihydro-6,8-dioxa-benzocycloheptene 

Downstream Products

• 28102-51-4 (4S*)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

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

Construction of Arene-Fused-Piperidine Motifs by Asymmetric Addition of 2-Trityloxymethylaryllithiums to Nitroalkenes: The Asymmetric Synthesis of a Dopamine D1 Full Agonist, A-86929

The straightforward methodology for the construction of chiral arene-fused-piperidine motifs using a highly enantioselective addition of 2-trityloxymethylaryllithiums to cyclic and acyclic nitroalkenes has been developed. The versatility of the process wa

Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol. A novel asymmetric route to 4-phenyl-1,2,3,4-tetrahydroisoquinolines

(equation presented) Highly diastereoselective protonation of chiral lactam enolates of 4-substituted-1,4-dihydroisoquinolin-3-ones is reported. Protonation and alkylation processes of these lactam enolates derived from phenylglycinol occur with opposite diastereofacial selectivity. This diastereoselective protonation has been applied to the asymmetric synthesis of (4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 9 obtained in up to 97% ee.

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.