Graveoline

Base Information

• Chemical Name: Graveoline
• CAS No.: 485-61-0
• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.295
• NSC Number: 603064
• DSSTox Substance ID: DTXSID80326593
• Nikkaji Number: J616.232K
• Wikidata: Q27106801
• Metabolomics Workbench ID: 46066
• ChEMBL ID: CHEMBL1371756
• Mol file: 485-61-0.mol

Synonyms:graveoline

Chemical Property of Graveoline

Chemical Property:

• Vapor Pressure: 7.91E-08mmHg at 25°C
• Melting Point: 204-205 °C
• Boiling Point: 436.7°Cat760mmHg
• PKA: 1.74±0.70(Predicted)
• Flash Point: 217.9°C
• PSA: 40.46000
• Density: 1.327g/cm³
• LogP: 2.93420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 279.08954328
• Heavy Atom Count: 21
• Complexity: 461

Purity/Quality:

97% ^*data from raw suppliers

Graveoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=O)C=C1C3=CC4=C(C=C3)OCO4
• Uses: Graveoline is an apoptosis and autophagy inducer in skin melanoma cancer cells.

Technology Process of Graveoline

There total 25 articles about Graveoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-(3,4-methylenedioxyphenyl)-1,4-dihydro-4-oxoquinoline (74054-38-9) + methyl iodide (74-88-4) → graveoline (485-61-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 5h; Inert atmosphere;

DOI:10.1080/00397911.2018.1501581

Reference yield: 63.0%

1-methyl-4-quinolone (83-54-5) + 5-iodo-1,3-benzodioxole (5876-51-7) → graveoline (485-61-0)

Guidance literature:

1-methyl-4-quinolone; With bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex; In tetrahydrofuran; at -20 ℃; for 48h; Inert atmosphere;

5-iodo-1,3-benzodioxole; With bis(dibenzylideneacetone)-palladium⁽⁰⁾; tris-(2-furyl)phosphine; In tetrahydrofuran; at 25 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ja306178q

Reference yield: 40.0%

Dubamine (6808-65-7) + methyl trifluoromethanesulfonate (333-27-7) → graveoline (485-61-0)

Guidance literature:

Dubamine; methyl trifluoromethanesulfonate; at 50 ℃; for 1h;

With sodium hydroxide; K₂Fe(CN)6; at 20 ℃; for 2h;

DOI:10.1248/cpb.47.1038

upstream raw materials:

methyl bisulfate

2-(3,4-methylenedioxyphenyl)-1,4-dihydro-4-oxoquinoline

1-(benzo[d][1,3]dioxol-6-yl)ethanone

N-Methylisatoic anhydride