15547-55-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE is used as a reactant in the preparation of isoquinoline libraries. These libraries are essential for the development of new pharmaceutical compounds, particularly those targeting the central nervous system. The compound's unique structure allows for the synthesis of a wide range of isoquinoline derivatives with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE serves as a valuable reactant for exploring various synthetic pathways and reaction mechanisms. Its use in the Bischler-Napieralski or Pictet-Spengler reactions, as well as in microwave-assisted variants of these reactions, provides researchers with valuable insights into the reactivity of isoquinoline derivatives and the potential for developing new synthetic methods.
Used in Material Science:
The compound's unique structure and properties may also find applications in material science, particularly in the development of novel materials with specific properties. For example, its potential use in the synthesis of conductive polymers or as a component in the development of new materials with specific optical, electronic, or mechanical properties could be explored.

Upstream product

• 15547-57-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 128741-53-7 [2-(2-Bromo-4,5-dimethoxy-phenyl)-ethyl]-[1-(3,4-dimethoxy-phenyl)-meth-(E)-ylidene]-amine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 142403-96-1 4,4-dimethyl-2-(3,4-dimethoxyphenyl)oxazolidine 
• 24456-59-5 6,7-dimethoxy-3,4-dihydroisoquinoline-1(2H)-thione 
• 24456-60-8 6,7-dimethoxy-1-(methylsulfanyl)-3,4-dihydroisoquinoline 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 33770-41-1 (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 93-07-2 Veratric acid 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 18034-37-2 N-<2-(3,4-dimethoxybenzyl)ethyl>-3,4-dimethoxybenzaldimine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 102011-15-4 N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide 
• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 

Downstream Products

• 22329-48-2 1-(3,4-dimethoxyphenyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 15547-57-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 879290-20-7 1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline N-oxide 
• 33770-43-3 (S)-1-1-(3',4'-dimethoxylphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 879290-24-1 10b-(3,4-dimethoxyphenyl)-8,9-dimethoxy-6,10b-dihydro-5H-isoxazolo[3,2-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester 
• 152561-03-0 Acetic acid 1-(3,4-dimethoxy-phenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl ester 

Relevant academic research and scientific papers

Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids

A new synthetic route was developed for the preparation of natural products cryptostyline I, II, III and 1-phenyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline. The Liebeskind-Srogl palladium-catalyzed carbon-carbon cross-coupling protocol was use

Effect of 1-Substitution on Tetrahydroisoquinolines as Selective Antagonists for the Orexin-1 Receptor

Selective blockade of the orexin-1 receptor (OX1) has been suggested as a potential approach to drug addiction therapy because of its role in modulating the brain's reward system. We have recently reported a series of tetrahydroisoquinoline-based OX1 selective antagonists. Aimed at elucidating structure-activity relationship requirements in other regions of the molecule and further enhancing OX1 potency and selectivity, we have designed and synthesized a series of analogues bearing a variety of substituents at the 1-position of the tetrahydroisoquinoline. The results show that an optimally substituted benzyl group is required for activity at the OX1 receptor. Several compounds with improved potency and/or selectivity have been identified. When combined with structural modifications that were previously found to improve selectivity, we have identified compound 73 (RTIOX-251) with an apparent dissociation constant (Ke) of 16.1 nM at the OX1 receptor and >620-fold selectivity over the OX2 receptor. In vivo, compound 73 was shown to block the development of locomotor sensitization to cocaine in rats. (Chemical Equation Presented).

Synthesis of Hydroxyethyl Derivatives of 1-Aryltetrahydroisoquinoline Alkaloids

New hydroxyethyl derivatives of 1-aryltetrahydroisoquinoline alkaloids and diisoquinoline were prepared using a Pictet-Spengler reaction.

Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method

Four racemic tetrahydroisoquinolines (RS)-(±)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.

Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

Three alkaloids of the cryptostylin series and 20 monomolecular and 3 bimolecular 1-aryltetrahydroisoquinoline derivatives were prepared using the Picte-Spengler reaction.

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.

Glycosylation-induced asymmetric synthesis of 1-substituted tetrahydroisoquinolines

Activation of imines by N-glycosylation and simultaneous diastereodifferentiation in reactions of the formed N-glycosyl iminium ions provide new stereoselective routes to 1-substituted tetrahydroisoquinolines. Pictet-Spengler reactions induced by N-galact

Synthesis of stable azomethine ylides by the rearrangement of 1,3-dipolar cycloadducts of 3,4-dihydroisoquinoline-2-oxides with DMAD

1-Aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines were prepared according to a one-pot procedure involving the reaction of 2-(3,4- dimethoxyphenyl)-ethylamine with aromatic aldehydes in TFA at reflux. The tetrahydroisoquinolines were treated with Hsub

Butyltriphenylphosphonium tetraborate (BTPPTB) as a selective reducing agent for the reduction of imines, enamines and oximes and reductive alkylation of aldehydes or ketones with primary amines in methanol or under solid-phase conditions

Butyltriphenylphosphonium tetraborate (BTPPTB) 1, generated as white solid from butyltriphenylphosphonium bromide and sodium borohydride, is found to be a selective and versatile reducing agent. The reagent in methanol or under solvent-free conditions is very useful for the reduction of imines, enamines and oximes or reductive amination of aldehydes and ketones. Under solvent-free conditions the reactions are faster and the yields of the products are higher.

Benzytriphenylphosphonium borohydride (BTPPB) as a selective reducing agent for reduction of imines, enamines, and reductive amination of aldehydes with primary and secondry amines in methanol

Benzyltriphenyltriphenylphosphonium borohydride (BTPPB) (1) generated as white solid from benzyltriphenylphosphonium chloride and sodium borohydride is found to be a selective and versatile reducing agent. The reagent in methanol is very useful for reduction of imines, enamines and reductive animation of aldehydes.