7058-95-9

Usage

Uses

Used in Pharmaceutical Applications:
(8S,13aS)-2,3,10,11-tetramethoxy-8-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline is used as a potential pharmaceutical agent for [application reason] due to its unique molecular structure and belonging to the isoquinoline alkaloid family. Further research is required to determine its specific applications and efficacy in the pharmaceutical industry.
Used in Chemical Research:
In the field of chemical research, (8S,13aS)-2,3,10,11-tetramethoxy-8-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline serves as a subject for studying the properties and potential applications of complex organic compounds, particularly within the isoquinoline alkaloid family. Its unique structure may provide insights into the development of new drugs or chemical processes.

Upstream product

• 109663-64-1 (8R,13R,13aS)-2,3,10,11-Tetramethoxy-8-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolin-13-ol 
• 123-63-7 paracetaldehyde 
• 308818-05-5 8-methylene-2,3,10,11-tetramethoxyberbine 
• 52050-59-6 2,3,9,10-tetramethoxy-8-oxoberbine 
• 59444-59-6 (+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 124293-98-7 1-(2'-bromo-4',5'-dimethoxybenzyl)-2-ethoxycarbonyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 109663-62-9 (13R,13aS)-13-Acetoxy-2,3,10,11-tetramethoxy-8-methyl-5,6,13,13a-tetrahydro-isoquino[3,2-a]isoquinolinylium; chloride 
• 109663-63-0 (+/-)-protoberberine 
• 62926-32-3 (+/-)-erythro-(O,N-diacetyl)hydroxynorlaudanosine 
• 1472637-58-3 C₂₀H₂₁NO₆ 
• 534-15-6 1,1-dimethoxyethane 
• 13074-31-2 Tetrahydropapaverine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6380-23-0 3,4-dimethoxystyrene 

Relevant academic research and scientific papers

HEXAHYDRODIBENZO[A,G]QUINOLIZINE COMPOUND, PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION AND USE THEREOF

The present invention relates to a novel hexahydrodibenzo[a,g]quinoline compound represented by general formula (I) and its derivatives, enantiomer, diastereoisomer, raceme and mixtures thereof, as well as pharmaceutically acceptable salts thereof. The pr

An approach to the synthesis of tetrahydroisoquinoline alkaloids by alkene hydroamination: Synthesis of coralydine

The protoberberine alkaloid coralydine was synthesized in a short sequence by a strategy including an intramolecular alkene hydroamination as the key step, followed by a Pictet-Spengler cyclization. Georg Thieme Verlag Stuttgart · New York.

Synthesis of 3,4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: Total synthesis of coralydine

(Chemical Equation Presented) Thanks to C-H activation: 3-Aryl-3,4-dihydroisoquinolines (2) are synthesized from bromobenzenes (1) by a sequence comprising a C(sp3)-H activation, a Curtius rearrangement, and a tandem electrocyclic ring-opening/

Enantioselective synthesis of some tetracyclic isoquinoline alkaloids by asymmetric transfer hydrogenation catalysed by a chiral ruthenium complex

Asymmetric transfer hydrogenation catalysed by chiral ruthenium complexes was the method for enantioselective synthesis of (R)-(+)-coralydine, (S)-(-)-homoprotoberberine, and (S)-(+)-homoaporphine in fair to excellent enantiomeric purity. Springer-Verlag 2005.

Benzolactams. 4. Reaction of 3′,4′- or 4′,5′-Dialkoxy-Substituted 1-(2′-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams

Treatment of 1-(2′-bromo-3′,4′-dialkoxybenzyl)-1,2,3,4- tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as MeLi or BuLi, gave a 1,2 addition product, 8-methyleneberbine 9a or 8-butylideneberbine 3a. t-BuLi preferred 1,4 addition, followed by elimination of the alkoxy group, to give 9-tert-butyl-8-oxoberbine 6a or 7c. s-BuLi gave a mixture of 1,2 and 1,4 addition products, 1-[2′-(2″-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4a and 9-s-butyl-8-oxoberbine 5a. Similar treatments of carbamate 1b having no alkoxy group at its 3′ position gave 1,2 addition products, 8-butylideneberbine 3b, 1-[2′-(2″-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4b, and 1-(2′-pivaloylbenzyl)-1,2,3,4-tetrahydroisoquinoline 6b, in all cases. Reactions of 1a with s-BuMgCl and isoPrMgCl also gave the 1,4 adduct, 5a, and its 9-isoPr analogue, 12a. Treatment of 9a with excess NaBH4 in AcOH gave (±)-coralydine (10b).

The Polonovski-Potier reaction of berbine N-oxides. Synthesis of 8-hydroxymethyl and 8-methylberbines

The Polonovski-Potier reaction of trans and cis berbines N-oxides was studied. The 8-cyano derivative obtained from trans N-oxides were used to synthesize 8-hydroxymethyl and 8-methyl berbines. This procedure was applied to the stereocontroled synthesis of (8R, 14S)-(-)-8-methylcanadine from (14S)-(-)-canadine. (C) 2000 Elsevier Science Ltd.

Bischler-napieralski cyclization-N/C-alkylation sequences for the construction of isoquinoline alkaloids. Synthesis of protoberberines and benzo[c]phenanthridines via C -2′-functionalized 3-arylisoquinolines

Efficient synthetic routes to isoquinoline alkaloids of the protoberberine and benzo[c]phenanthridine classes are reported. The key transformations are derived from the intramolecular cyclization of C-2'-functionalized N-(1,2-diarylethyl)amides or enamides via 3-arylisoquinoline derivatives. Thus, under Bischler-Napieralski reaction conditions (PCl5, nitrile as solvent, room temperature) N-(1,2-diarylethyl)amides 12 regioselectively yielded 2,3-disubstituted 13,14-dihydroprotoberberinium salts 20, a scarcely studied oxidation state in this class of alkaloids. Subsequent reduction of the iminium bond gave the known coralydine (21a) and O-methylcorytenchirine (21b) and their 8-phenyl analogue 21c. The one-pot preparation of these dihydroprotoberberinium salts 20 is shown to proceed with cleavage of the silyl ether and immediate halogenation of the resulting hydroxyl group, followed by cyclization of the obtained AT-(1,2-diarylethyl)amide 18 to a 3,4-dihydroisoquinoline derivative 19 and subsequent intramolecular in situ N-alkylation of the latter imine. Ready access to planar 8,9-dialkoxylated benzo[c]phenanthridinium salts is also described. Condensation of ketoester 23 with benzylamine in the presence of titanium(IV) chloride, followed by acetylation, afforded a mixture of naphthylamide 24 and (E)-enamide 25. Both enamides were efficiently cyclized by POCI3. While the planar benzo[c]phenanthridinium salt 26 was directly produced from 24, the (E)-enamide 25 gave the 3-arylisoquinolinium salt 27, which was reduced and intramolecularly C-alkylated to yield the tetracyclic nucleus of these alkaloids.