56030-50-3

Usage

InChI:InChI=1/C19H23NO2/c1-20-10-9-15-11-18(21-2)19(22-3)12-16(15)17(13-20)14-7-5-4-6-8-14/h4-8,11-12,17H,9-10,13H2,1-3H3/t17-/m1/s1

Upstream product

• 20012-08-2 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 127239-58-1 (+)-(S)-2-{t-butoxycarbonyl(methyl)amino}-1-phenylethanol 
• 65058-52-8 N-methyl (S)-2-hydroxy-2-phenylethylamine 
• 17199-29-0 (S)-Mandelic acid 
• 20569-49-7 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 

Downstream Products

• 81633-75-2 (R)-3-cyano-2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-1H-3-benzazepine 
• 62717-63-9 (R)-2,3,4,5-tetrahydro-7,8-dihydroxy-3-methyl-1-phenyl-1H-3-benzazepine hydrobromide 
• 139689-19-3 (+)-6-Br-APB hydrobromide 
• 139689-16-0 (R)-(+)-3-allyl-6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 139689-08-0 (R)-(+)-3-allyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 139689-14-8 (R)-(+)-6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 139689-12-6 (R)-(+)-3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 81702-42-3 (+)-SKF 38393 hydrochloride 
• 62717-90-2 (1R)-(+)-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 

Relevant academic research and scientific papers

Stereoisomeric probes for the D1 dopamine receptor: synthesis and characterization of R-(+) and S-(-) enantiomers of 3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine and its 6-bromo analogue.

Substituted 1-phenyl-3-benzazepines (e.g., SKF 38393 and fenoldopam) exhibit stereoselectivity in moderately high-affinity binding to and partial agonist activation of D1 dopamine receptors. The 3-allyl (APB) and the 3-allyl-6-chloro (6-Cl-APB) analogues

Tricarbonylchromium(0) Promoted Stereoselective Cyclisations of the N-3,4-Dimethoxyphenethyl Derivatives of the 1-Phenyl Ethanolamines Halostachine, Ephedrine and Pseudoephedrine to 1-Phenyl-N-Methyl-7,8-Dimethoxy-1,2,4,5-Tetrahydrobenzazepines

Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl)-halostachine proceeds with almost total racemisation to yield 1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine (e.e, 6percent).Coordination of the cyclisation precursor to the tricarbonylchromium(0) moiety renders the cyclisation completely stereospecific to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine. (-)-(1R,2S)-N-(3,4-Dimethoxyphenethyl)ephedrine undergoes acid mediated cyclisation to furnish trans-(-)-(1R,2S)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine as a single diastereoisomer.In contrast, the epimeric cyclisation precursor (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine cyclises to give a mixture (ratio 91:9) of trans- and cis-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine.However, cyclisation of the tricarbonylchromium(0) complex of (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudo-ephedrine is completely stereoselective to yield trans-(+)-(1S,2R)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine after decomplexation.

ENANTIOSPECIFIC SYNTHESIS OF (+)-(R)-1-PHENYL-3-METHYL-1,2,4,5-TETRAHYDROBENZAZEPINE FROM (+)-(S)-N-METHYL-1-PHENYL ETHANOLAMINE (HALOSTACHINE) via ARENE CHROMIUM TRICARBONYL METHODOLOGY

Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl) halostachine chromium tricarbonyl is stereospecific, proceeding with retention of configuration, to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-3-methyl-1,2,4,5-tatrahydr

Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine

Resolution of the unique dopamine receptor agonist 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine (1) was achieved by a stereospecific multistep conversion of the readily separated enantiomers of its O,O,N-trimethylated diffractometric analysi