80041-81-2

Basic information

• Product Name: Isoquinoline, 1-[(2-bromophenyl)methyl]-3,4-dihydro-6,7-dimethoxy-
• CAS NO: 80041-81-2
• Molecular Formula: C18H18BrNO2
• Molecular Weight: 360.25
• Mol File: 80041-81-2.mol

Chemical Properties

• CAS DataBase Reference: Isoquinoline, 1-[(2-bromophenyl)methyl]-3,4-dihydro-6,7-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 1-[(2-bromophenyl)methyl]-3,4-dihydro-6,7-dimethoxy-(80041-81-2)
• EPA Substance Registry System: Isoquinoline, 1-[(2-bromophenyl)methyl]-3,4-dihydro-6,7-dimethoxy-(80041-81-2)

Safety Data

• Hazardous Substances Data: 80041-81-2(Hazardous Substances Data)

Upstream product

• 18698-97-0 ortho-bromophenylacetic acid 
• 55116-09-1 2-bromophenylacetyl chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 109558-14-7 β-(3,4-dimethoxyphenyl)ethyl-(2'-bromophenyl)acetamide 

Downstream Products

• 934355-85-8 (R)-1-(2-bromobenzyl)-1,2,3,4-tetrahydro-6,7-dimethoxyiaoquinoline 
• 934355-86-9 (R)-methyl 1-(2-bromobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate 
• 934355-87-0 (R)-tert-butyl 1-(2-bromobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate 
• 839673-82-4 1-(2'-bromobenzyl)-N-tert-butyloxycarbonyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 934355-54-1 C₂₀H₂₂BrNO₄ 
• 839673-87-9 C₂₀H₂₂BrNO₃ 
• 839673-88-0 C₂₅H₂₆BrNO₄S 
• 69424-55-1 1,2-demethylnuciferine 
• 754919-24-9 C₂₀H₂₄NO₂⁽¹⁺⁾ 
• 5531-98-6 atherosperminine 
• 1491132-43-4 1-(2-bromophenyl)-9,10-dimethoxy-2-methyl-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-4-one 
• 1491132-45-6 11B-(2-bromobenzyl)-9,10-dimethoxy-2-methyl-7,11b-dihydro-4H,6H-[1,3]oxazino[2,3-a]isoquinolin-4-one 
• 78946-24-4 1-(2-bromobenzyl)-N-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 47206-72-4 2,3-dimethoxyberbine 

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.

1-(2′-Bromobenzyl)-6,7-dihydroxy- N-methyl-tetrahydroisoquinoline and 1,2-Demethyl-nuciferine as Agonists in Human D2 Dopamine Receptors

Certain D2-like dopamine receptor (DR) agonists are useful therapeutically as antiparkinsonian drugs, whereas D2-like DR antagonists or partial agonists are proven effective as antipsychotics. Two isoquinoline derivatives, 1-(2′-brom

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.

3,4-Dihydroxy- and 3,4-methylenedioxy- phenanthrene-type alkaloids with high selectivity for D2 dopamine receptor

Dopamine-mediated neurotransmission plays an important role in relevant psychiatric and neurological disorders. Nowadays, there is an enormous interest in the development of new drugs acting at the dopamine receptors (DR) as potential new targets for the

Synthesis of pyrido[2,1-a]isoquinolin-4-ones and oxazino[2,3-a]isoquinolin- 4-ones: New inhibitors of mitochondrial respiratory chain

Benzo[a]quinolizine is an important heterocyclic framework that can be found in numerous bioactive compounds. The general scheme for the synthesis of these compounds was based on the preparation of the appropriate dihydroisoquinolines by Bischler-Napieral

Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams

Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright

Total syntheses of telisatin A, telisatin B and lettowianthine

Treatment of 1-(2-bromoarylmethyl)-3,4-dihydroisoquinolines with oxalyl chloride and triethylamine gave 1-(2-bromophenyl)-5,6-dihydropyrrolo[2,1-a] isoquinoline-2,3-dione derivatives, for example, 1-(2-bromophenyl)-5,6-dihydro- 8,9-dimethoxypyrrolo[2,1-a]

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.

One-pot formation of nitrogen-containing heterocyclic ring systems using a deprotection-cyclisation-asymmetric reduction sequence

A one-pot sequence of amine deprotection, intramolecular C=N bond formation and subsequent asymmetric reduction may be promoted by a ruthenium catalyst. The Royal Society of Chemistry 2005.

Antiplatelet activity of synthetic pyrrolo-benzylisoquinolines

Pyrrolo-benzylisoquinolines were prepared as target compounds and their antiplatelet aggregation activity, adreno-receptor affinity, and cytotoxicity were screened. Compounds 1d-9d showed specific antiplatelet aggregation activity induced by arachidonic acid and collagen. Among them, 8d and 9d exhibited better activity than the reference drug, aspirin and 9d also showed inhibition of platelet aggregation by all four inducers.