87201-31-8

Basic information

• Product Name: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline
• Synonyms: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline
• CAS NO: 87201-31-8
• Molecular Weight: 344.208
• Mol File: 87201-31-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline(87201-31-8)
• EPA Substance Registry System: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline(87201-31-8)

Safety Data

• Hazardous Substances Data: 87201-31-8(Hazardous Substances Data)

Upstream product

• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 19472-74-3 2-(2-bromophenyl)acetonitrile 
• 6006-82-2 3,4-methylenedioxyphenethyl alcohol 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 7154-66-7 2-bromobenzoic acid chloride 
• 46004-44-8 2-bromo-ω-diazoacetophenone 
• 55116-09-1 2-bromophenylacetyl chloride 
• 18698-97-0 ortho-bromophenylacetic acid 
• 87201-30-7 N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide 

Downstream Products

• 475-75-2 liriodenine 
• 934355-59-6 tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate 
• 548-08-3 (+)-roemerine 
• 1187077-78-6 1-(2-bromophenyl)-5,6-dihydro-8,9-methylenedioxypyrrolo[2,1-a]isoquinoline-2,3-dione 
• 87489-86-9 1-(2'-bromo-α-hydroxybenzyl)-6,7-methylenedioxyisoquinoline 
• 87489-85-8 (2-bromophenyl)([1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 934355-48-3 5-(2-bromobenzyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline 
• 76525-21-8 (2-bromophenyl)(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 87201-32-9 ethyl (Z)-1-(2-bromobenzylidene)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 

Relevant articles and documents

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

In this study, the (S)-enantiomers of the aporphine alkaloids, nuciferine and roemerine, were prepared via a synthetic route involving catalytic asymmetric hydrogenation and both stereoisomers were evaluated in vitro for functional activity at human 5-HT2 and adrenergic α1 receptor subtypes using a transforming growth factor-α shedding assay. Both enantiomers of each of the compounds were found to act as antagonists at 5-HT2 and α1 receptors. (R)-roemerine was the most potent compound at 5-HT2A and 5-HT2C receptors (pKb = 7.8-7.9) with good selectivity compared to (S)-roemerine at these two receptors and compared to its activity at 5-HT2B, α1A, α1B and α1D receptors.

Aporphine alkaloid synthesis and diversification via direct arylation

Palladium-catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2-substituted aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.