62595-72-6

Basic information

• Product Name: 9,10-dimethoxy-5,13a-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-13-ol
• Synonyms: 13-hydroxy-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium
• CAS NO: 62595-72-6
• Molecular Formula: C₂₀H₁₇NO₅
• Molecular Weight: 352.3601
• Mol File: 62595-72-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9,10-dimethoxy-5,13a-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-13-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-dimethoxy-5,13a-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-13-ol(62595-72-6)
• EPA Substance Registry System: 9,10-dimethoxy-5,13a-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-13-ol(62595-72-6)

Safety Data

• Hazardous Substances Data: 62595-72-6(Hazardous Substances Data)

Upstream product

• 483-15-8 7,8-dihydroberberine 

Downstream Products

• 21796-14-5 noroxyhydrastinine 
• 66408-38-6 1-(2-carboxy-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinoline 
• 71766-69-3 13a-hydroxy-9,10-dimethoxy-2,3-(methylenedioxy)-8,13-dioxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine 
• 71734-53-7 1,2,3,4-tetrahydro-1-(3,4-dimethoxy-2-methoxycarbonylbenzoyl)-2-methyl-6,7-(methylenedioxy)isoquinoline 
• 66408-37-5 3,4-dihydro-1-(3,4-dimethoxy-2-methoxycarbonylbenzoyl)-2-methyl-6,7-(methylenedioxy)isoquinolinium iodide 
• 75523-07-8 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one 
• 75509-67-0 3,4-dihydro-(3,4-dimethoxy-2-methoxycarbonylbenzoyl)-6,7-(methylenedioxy)isoquinoline 
• 1160707-16-3 13-benzyloxy-9,10-dimethoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium bromide 
• 1160707-17-4 13-(4-cyanobenzyloxy)-9,10-dimethoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium bromide 

Relevant articles and documents

A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.

Reaction of Protoberberine-type Alkaloids. Part 12. A Facile Method for Regiospecific Oxygenation and Excited Oxidative Ring-cleavage of Berberine Alkaloids

Regiospecific photo-oxygenation and photo-oxidative ring-cleavage of protoberberine alkaloids is described.Irradiation of a solution of dihydroberberine (1) in the presence of Rose Bengal under aerated conditions gave 13-oxidoberberine (3) along with berberine (2) in 80 and 7percent yields, respectively.In contrast, 7,8-dihydrocoralyne (5) gave 13-oxidocoralyne (7) in nearly quantitative yield when an aerated solution of (5) was heated in the dark.Irradiation of a solution of (3) containing Rose Bengal with visible light afforded 8,13a-epidioxy-9,10-dimethoxy-2,3-(methylenedioxy)- 13-oxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (11) in 90percent yield.Under the same conditions, however, (7) gave 2'-acetylpapaveraldine (14) in 88percent yield.On the other hand, when an alcoholic solution of (5) or (7) containing sodium alkoxide was irradiated with a mercury lamp (Vycol filter) under bubbling oxygen, 6,7-dimethoxyisoquinolone (16) and 3-alkoxy-5,6-dimethoxy-3-methylisobenzofuran-1(3H)-one (17) or (18) were obtained in moderate yields.A reaction mechanism which involves the initial formation of an epidioxy-intermediate was evidenced by the fact that the photolysis of (7) was carried out in the presence of borohydride anion to give (16) and 5,6-dimethoxy-3-methylisobenzofuran-1(3H)-one (19).Irradiation of (11) in the same fashion gave berberal (20) and 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one (21) in 72percent and 4percent yields, respectively.Possible mechanisms are also presented.Reduction of (3) with sodium borohydride gave (+/-)-ophiocarpine (9) and (+/-)-13-epiophiocarpine (10), with the ratio (9):(10) varying depending upon the nature of the alcohol used as solvent.An interpretation which rationalizes these observations is suggested.