5140-38-5

Basic information

• Product Name: Homomoschatoline
• Synonyms: Homomoschatoline;1,2,3-Trimethoxy-7H-dibenzo[de,g]quinolin-7-one;Liridine;O-Methylmoschatoline
• CAS NO: 5140-38-5
• Molecular Formula: C19H15 N O4
• Molecular Weight: 321.33
• Mol File: 5140-38-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 271-273 °C
• Boiling Point: 528.4°C at 760 mmHg
• Flash Point: 273.3°C
• Appearance: /
• Density: 1.315g/cm³
• Vapor Pressure: 2.99E-11mmHg at 25°C
• Refractive Index: 1.657
• PKA: 2.43±0.20(Predicted)
• CAS DataBase Reference: Homomoschatoline(CAS DataBase Reference)
• NIST Chemistry Reference: Homomoschatoline(5140-38-5)
• EPA Substance Registry System: Homomoschatoline(5140-38-5)

Safety Data

• Hazardous Substances Data: 5140-38-5(Hazardous Substances Data)

Usage

Description

This oxo-proaporphine alkaloid has now been discovered in both A buta imene and A. rufeocens, being found chiefly in the stems.

References

Caveetal., Tetrahedron, 31,1667 (1975)

InChI:InChI=1/C19H15NO4/c1-22-17-12-8-9-20-15-13(12)14(18(23-2)19(17)24-3)10-6-4-5-7-11(10)16(15)21/h4-9H,1-3H3

Upstream product

• 3937-16-4 2-(2,3,4-trimethoxyphenyl)ethylamine 
• 118474-94-5 (E)-1-nitro-2-(2',3',4'-trimethoxyphenyl)ethene 
• 5667-97-0 5,6,7-trimethoxy-1-(2-nitro-benzyl)-3,4-dihydro-isoquinoline 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 5531-84-0 N-(2,3,4-trimethoxyphenethyl)-2-(2-nitrophenyl)acetamide 
• 186581-53-3 diazomethane 
• 83375-15-9 isomoschatoline 

Relevant articles and documents

AZAFLUORENONES AND AZAANTHRAQUINONE FROM GUATTERIA DIELSIANA

Trunkwood of Guatteria dielsiana afforded eight alkaloids and one triterpene.Three of the alkaloidal constituents are oxoaporphines: liriodenine, O-methylmoschatoline and isomoschatoline; four are 1-azafluorenones: onychine, the only previously known representative of this group, and three novel compounds of this rare type, 6-methoxyonychine, dielsine (1-aza-4-methyl-2-oxo-1,2-dihydrofluorenone) and dielsinol (1-aza-4-hydroxymethyl-2-oxo-1,2-dihydrofluorenone).The last alkaloid is dielsiquinone (1-aza-3-methoxy-4-methyl-2-oxo-1,2-dihydro-9,10-anthrachenedione), the second representative of a new class of quinones of which cleistopholine was the only one previously known.The triterpene is polycarpol whose presence is of chemotaxonomic significance since this metabolite seems to be exclusive to the Annonaceae.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.