103769-59-1

Basic information

• Product Name: corrunine
• Synonyms: corrunine
• CAS NO: 103769-59-1
• Molecular Weight: 351.359
• Mol File: 103769-59-1.mol

Chemical Properties

• CAS DataBase Reference: corrunine(CAS DataBase Reference)
• NIST Chemistry Reference: corrunine(103769-59-1)
• EPA Substance Registry System: corrunine(103769-59-1)

Safety Data

• Hazardous Substances Data: 103769-59-1(Hazardous Substances Data)

Upstream product

• 5630-11-5 (+/-)-glaucine 
• 55974-08-8 oxoglaucine methiodide 
• 5574-24-3 oxoglaucine 
• 74-88-4 methyl iodide 
• 103769-57-9 3,4,6,7-Tetramethoxy-1-(2-methylamino-ethyl)-phenanthrene-9,10-dione 
• 103769-50-2 secoroemerine 
• 83511-44-8 1-(2'-amino-4',5'-dimethoxy-α-oxobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 38726-64-6 tetradehydroglaucine 

Relevant articles and documents

SOURCE OF SOME MINOR ALKALOIDS IN GLAUCIUM FLAVUM

Air oxidation of glaucine leads to 7,6'-dehydroglaucine and 1,2,9,10-tetramethoxyoxoaporphine, and UV irradiation gives dihydropontevedrine, pontevedrine, glaucine-N-oxide and corunine.These results support the view that glaucine, the main alkaloid in Glaucium flavum, may produce all the more oxidized minor alkaloids present in the plant.Key Word Index-Glaucium flavum; Papaveraceae; alkaloids; glaucine; air oxidation; UV irradiation; dihydropontevedrine.

Manganese(III) acetate mediated oxidation of aporphines: a convenient and useful synthesis of oxoaporphines

Manganese(III) acetate mediated oxidation of aporphines to oxoaporphines is described. The developed methodology was conveniently applied for the synthesis of naturally occurring oxoaporphine alkaloids, oxoglaucine, and atheroline, starting from commercially available boldine.

A DIRECT CONVERSION OF PHENANTHRENES TO APORPHINOIDS

We desribe a single-step conversion of phenanthrene alkaloid derivatives into oxoaporphines based on the cyclization of 9,10-phenanthrenediones with ethanamine side-chains under basic conditions.

PHOTOCHEMICAL SYNTHESIS AND REACTIVITY OF TETRADEHYDROAPORPHINES

An efficient method to prepare 4,5,6a,7-tetradehydroaporphines is described.It is based on the photoreduction of benzophenone by amines.Oxidation of 4,5,6a,7-tetradehydroaporphines under several conditions gave oxoaporphines.

Hofmann Degradation of β-Hydroxy Ammonium Salts. α- and β-Hydroxylaudanosine, 7-Hydroxyglaucine, and 13-Hydroxyxylopinine

The four related β-hydroxy ammonium methiodide salts of α-hydroxylaudanosine (2a), β-hydroxylaudanosine (2b), 7-hydroxyglaucine (5a), and 13-hydroxyxylopinine (8a) have been subjected to Hofmann degradation.Although precedent dictates that such materials should form either epoxides or ketones, these are not found.Only products of (a) fragmentation and elimination (from 2a and 2b), (b) dehydration and elimination (from 5a), and (c) elimination and oxidation (from 8a) are obtained.The results are accounted for by consideration of the molecular geometries of theβ-hydroxy ammonium salts as experimentally determined from single-crystal X-ray studies and the geometric requirements for epoxide and ketone formation.

Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids

Liriodenine was evaluated for its antibacterial and antifungal activity against several microorganisms. Other related oxoaporphine alkaloids also were evaluated. Attempts to prepare oxoaporphine alkaloids from N-acetylnoraporphines were unsuccessful, but an unexpected phenanthrene alkaloid was obtained. A novel N-demethylation reaction was noted when oxoglaucine methiodide and liriodenine methiodide were treated with alumina.

The SYNTHESIS OF ERYTHRO- AND THREO-N-METHYL 7-HYDROXY-1,2,9,10-TETRAMETHOXYAPORPHINE

The total synthesis of the title compounds is described.