485-61-0

Basic information

• Product Name: GRAVEOLINE
• Synonyms: 1-methyl-2-[3',4'-(methylenedioxy)phenyl]-4-quinolone;2-(Benzo[d][1,3]dioxol-5-yl)-1-methylquinolin-4(1H)-one;2-(1,3-benzodioxol-5-yl)-1-methylquinolin-4-one
• CAS NO: 485-61-0
• Molecular Formula: C17H13NO3
• Molecular Weight: 279.294
• Mol File: 485-61-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 204-205 °C
• Boiling Point: 436.7°Cat760mmHg
• Flash Point: 217.9°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 7.91E-08mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.74±0.70(Predicted)
• CAS DataBase Reference: GRAVEOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: GRAVEOLINE(485-61-0)
• EPA Substance Registry System: GRAVEOLINE(485-61-0)

Safety Data

• Hazardous Substances Data: 485-61-0(Hazardous Substances Data)

Usage

Uses

Graveoline is an apoptosis and autophagy inducer in skin melanoma cancer cells.

InChI:InChI=1/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3

Upstream product

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 10328-92-4 N-Methylisatoic anhydride 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 6630-33-7 ortho-bromobenzaldehyde 
• 94-53-1 Piperonylic acid 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 4179-37-7 graveolinine 
• 83-54-5 1-methyl-4-quinolone 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 40141-72-8 N-phenylbenzo[d][1,3]dioxole-5-carboxamide 
• 94301-36-7 2-benzo[1,3]dioxol-5-yl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 93329-02-3 2-benzo[1,3]dioxol-5-yl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 62-53-3 aniline 

Relevant articles and documents

4(1H)-quinolinone alkaloids an efficient synthesis of graveoline by palladium-catalysed reductive N-heterocyclisation

An efficient synthesis of the 4H-quinolone alkaloid graveoline has been achieved by a route featuring an Pd(II)-catalysed reductive N-heterocyclisatton [ CO(3 MPa), Pd(TMB)2, TMPhen, 170 °C, 3h] of 2′-nitrochalcone as a key step.

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.

Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones

A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl2, a C(3) zincation is observed, whereas in the presence of MgCl2 or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.