85611-40-1

Usage

Uses

Used in Pharmaceutical Industry:
(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline is used as a precursor in organic synthesis for the development of new pharmaceuticals, leveraging its unique molecular structure and potential pharmacological properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline serves as a valuable compound for studying its interactions with biological targets and exploring its potential therapeutic applications.
Used in Pharmacology Studies:
Pharmacologists utilize (1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline to investigate its effects on various physiological processes and to assess its safety and efficacy as a potential drug candidate.
Used in Organic Chemistry Synthesis:
Organic chemists employ (1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline as a key intermediate in the synthesis of more complex organic molecules, taking advantage of its reactive functional groups and structural features.

Upstream product

• 186581-53-3 diazomethane 
• 56114-05-7 1-<2-(4-hydroxy-3-methoxy)ethyl>-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 20226-10-2 1-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium iodide 
• 51842-87-6 3-(3,4-dimethoxy-phenyl)-propionyl chloride 
• 20944-13-2 N-<2-(3,4-dimethoxyphenyl)ethyl>-3-(3,4-dimethoxyphenyl)propionamide 
• 111427-24-8 N-<3-(3,4-dimethoxyphenyl)propionyl>-2-thiazolidine-2-thione 
• 1374870-00-4 6,7-dimethoxy-1-(3,4-dimethoxyphenylethynyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 4302-52-7 4-ethynylveratrole 
• 123190-12-5 2-(2-bromoethyl)-4,5-(dimethoxy)benzaldehyde 
• 50-00-0 formaldehyd 
• 65899-28-7 1,2,3,4-tetrahydro-6,7-dimethoxy-1<2-(3,4-dimethoxyphenyl)ethyl>isoquinoline 
• 79631-01-9 1,2-dimethoxy-4-<1-<(1,1-dimethylethyl)dimethylsilyloxy>ethenyl>benzene 
• 64728-23-0 2-(3,4-dimethoxyphenyl)-1-iodoethane 

Downstream Products

• 97117-83-4 3-(3,4-Dimethoxy-phenyl)-1-<4,5-dimethoxy-2-<2-(methyl-aethoxycarbonyl-amino)-aethyl>-phenyl>-propen-(1) 
• 105578-49-2 (+/-)-N,N-Dimethyl-6,7,3',4'-tetramethoxyphenylethyl-1,2,3,4-tetrahydroisoquinolinium iodide 

Relevant academic research and scientific papers

Asymmetric synthesis of six tetrahydroisoquinoline natural products through α-amination of an aldehyde

An enantioselective route towards the synthesis of C-1 substituted tetrahydroisoquinoline natural products is reported. Six different natural products are synthesized from a single aldehyde using proline-catalyzed asymmetric α-hydrazination reaction as th

Biomimetic Total Synthesis of Dysoxylum Alkaloids

A five-step total synthesis of Dysoxylum alkaloids has been achieved using a biomimetic approach from zanthoxylamide protoalkaloids. The synthesis featured a direct amidation and a Bischler-Napieralski reaction to form the dihydroisoquinoline ring, which

Succinct Syntheses of Methopholine, (±)-Homolaudanosine, and (±)-Dysoxyline via Metal-free One-Pot Double Alkylation on 1-Methyl-3,4-dihydroisoquinolines

A mild one-pot and metal-free condition was discovered to implement two different alkyl groups chemoselectively on 1-methyl-3,4-dihydroisoquinoline (1-Me-DHIQ), one at the nitrogen another at the C1-methyl group. This chemistry is compatible with various DHIQs as well as alkyl halides. Application of this chemistry facilitated the concise syntheses of methopholine, (±)-homolaudanosine, and (±)-dysoxyline, requiring only two steps from 6,7-dimethoxy-1-Me-DHIQ.

Unified approach to isoindolinones and THIQs via lewis acid catalyzed domino mukaiyama-mannich Lactamization/Alkylations: Application in the synthesis of (±)-homolaudanosine

A novel and efficient synthesis of a variety of isoindolinones and tetrahydroisoquinolines via a Lewis acid catalyzed domino Mukaiyama-Mannich lactamization/alkylation is achieved. This transformation comprises a sequential formation of three new bonds through a one-pot, three-component procedure to afford product in moderate to high yields. A concise synthesis of (±)-homolaudanosine (2b) has been achieved using this method.

C-1 alkynylation of N-methyltetrahydroisoquinolines through CDC: A direct access to phenethylisoquinoline alkaloids

Direct cross-coupling between N-methyltetrahydroisoquinolines and alkynes using CuI-DEAD is presented. It affords the regioselective C-1-alkynylated products in good yield. This regio-selectivity is in contrast to the results reported earlier in the reaction of N,N-dimethylbenzyl amine where the N-methyl alkynylated product was formed exclusively or predominantly. The C-1-substituted propargylic isoquinolines were easily reduced to phenethylisoquinolines with Pd/C. This reaction sequence provides a short route to synthesize methopholine, homolaudanosine and other phenethylisoquinoline alkaloids. Georg Thieme Verlag Stuttgart · New York.

Catalytic asymmetric allylation of 3,4-dihydroisoquinolines and its application to the synthesis of isoquinoline alkaloids

A catalytic asymmetric allylation of 3,4-dihydroisoquinoline was carried out with allyltrimethoxylsilane-Cu as the nucleophile in the presence of DTBM-SEGPHOS as the chiral ligand to afford corresponding chiral 1-allyltetrahydroisoquinoline derivatives in good yield and stereoselectivity. The allyl adduct thus obtained was applied to the synthesis of several isoquinoline alkaloids such as crispine A and homolaudanosine. The reaction was further used for the synthesis of the isoquinoline moiety of schulzeine A.

Synthesis and radioligand binding studies of methoxylated 1,2,3,4-tetrahydroisoquinolinium derivatives as ligands of the apamin-sensitive Ca2+-activated K+ channels

Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinit

Enantioselective addition of terminal alkynes to isolated isoquinoline iminiums

(Chemical Equation Presented) The asymmetric, catalytic addition of terminal alkynes to discrete alkyliminium species in the presence of copper bromide, QUINAP ligand, and triethylamine is reported. The reaction proceeds in high yield and high enantiomeri

Ruthenium dioxide in fluoro acid medium. III. Aplication to the synthesis of aporphinic, homoaporphinic and dibenzazocinic alkaloids. Studies towards the preparation of azafluoranthenic skeleton

Intramolecular oxidative couplings of phenylalkyltetrahydroisoquinoline precursors in aporphinic and homoaporphinic alkaloids by using RuO2,2H2O in fluoro acidic media were performed. A comparative study of our reagent with TTFA has been made with different precursors. The procedure was also extended to the synthesis of one dibenzazocinic alkaloid. Then, we attempted to synthetize the azafluoranthenic ring, using phenolic and non phenolic isoquinoline precursors.

Recent progress using chiral formamidines in asymmetric syntheses

The ability to generate a carbanion next to nitrogen in a chiral environment has led to a number of useful asymmetric routes to alkaloids and related substances. Mechanistic studies have been conducted to understand the nature of these alkylations.