75523-07-8

Basic information

• Product Name: 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one
• Synonyms: 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one
• CAS NO: 75523-07-8
• Molecular Weight: 383.357
• Mol File: 75523-07-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one(75523-07-8)
• EPA Substance Registry System: 2-(2-formyl-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinolin-1(2H)-one(75523-07-8)

Safety Data

• Hazardous Substances Data: 75523-07-8(Hazardous Substances Data)

Upstream product

• 62595-72-6 berberinephenolbetaine 
• 483-15-8 7,8-dihydroberberine 
• 64939-63-5 8,13a-epidioxy-9,10-dimethoxy-2,3-(methylenedioxy)-13-oxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine 

Relevant articles and documents

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.