68858-27-5

Usage

Chemical class

Dibenzoazocines, a type of organic compound.

Molecular weight

323.43 g/mol

Structure

Bicyclic, with two benzene rings fused with an azocine ring.

Substitution

Contains a phenyl group attached to the 12th carbon atom.

Biological activity

Potent opioid receptor ligand.

Therapeutic use

Exhibits strong analgesic properties, of interest in pharmaceutical research.

Psychoactive potential

Interactions with the central nervous system, studied for its potential as a psychoactive agent.

Upstream product

• 137522-29-3 2-Benzyl-4-phenyl-1,2,3,4-tetrahydro-isoquinolin-4-ol 
• 24431-24-1 2-(dibenzylamino)-1-phenylethan-1-one 
• 103-49-1 dibenzylamine 
• 131326-81-3 2-[Benzyl-(2-iodo-benzyl)-amino]-1-phenyl-ethanone 
• 56008-40-3 N-benzyl-1-(2-iodophenyl)methanamine 
• 70-11-1 α-bromoacetophenone 
• 37481-70-2 2-Benzyl-4-phenyl-1,2,3,4-tetrahydro-isoquinolin-4-ol; hydrochloride 

Relevant academic research and scientific papers

Synthesis of 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines via N,N-dibenzylphenacylamines

N,N-DibenzyIphenacylamines (1) were prepared in high yields by a onepot reaction and cyclized at room temperature to give 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cyclization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (If) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However la gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid at room temperature.

A NEW SYNTHESIS OF 7,12-DIHYDRO-12-PHENYL-5H-6,12-METHANODIBENZAZOCINES VIA N-BENZYL-1,2,3,4-TETRAHYDRO-4-PHENYLISOQUINOLIN-4-OLS

7,12-Dihydro-12-phenyl-5H-6,12-methanodibenzazocine derivatives were prepared from N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinolin-4-ols by an intramolecular Friedel-Crafts reaction.

ACID-CATALYZED DOUBLE-CYCLIZATION REACTIONS OF N,N-DIBENZYLAMINO-ACETALDEHYDE DIALKYL ACETALS AND RELATED COMPOUNDS: GENERAL SYNTHESIS OF 7,12-DIHYDRO-5H-6,12-METHANODIBENZAZOCINES AND RELATED COMPOUNDS

A number of N,N-dibenzylaminoacetaldehyde dialkyl acetals (1) double-cyclized in 70percent perchloric acid or triflic acid (trifluoromethanesulfonic acid) to give good yields of 7,12-dihydro-5H-6,12-methanodibenzazocines (2) even when a powerful elec