Methoxatin trimethyl ester

Base Information

• Chemical Name: Methoxatin trimethyl ester
• CAS No.: 74447-88-4
• Molecular Formula: C17H12 N2 O8
• Molecular Weight: 372.291
• DSSTox Substance ID: DTXSID50225463
• Nikkaji Number: J434.362J
• Wikidata: Q83104433
• Mol file: 74447-88-4.mol

Synonyms:Methoxatin trimethyl ester;74447-88-4;PQQ trimethyl ester;Coenzyme PQQ trimethyl ester;PQQ-TME;trimethyl 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate;1H-Pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-, trimethyl ester;Trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate;4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester;trimethyl 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate;SCHEMBL1992364;DTXSID50225463;Pyrroloquinoline quinone trimethyl;C17H12N2O8;C17-H12-N2-O8;LS-139699;4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

Chemical Property of Methoxatin trimethyl ester

Chemical Property:

• Vapor Pressure: 6.45E-17mmHg at 25°C
• Boiling Point: 652.7°C at 760 mmHg
• Flash Point: 348.5°C
• PSA: 141.72000
• Density: 1.523g/cm³
• LogP: 0.81550
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 372.05936535
• Heavy Atom Count: 27
• Complexity: 692

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=NC2=C1C3=C(C=C(N3)C(=O)OC)C(=O)C2=O)C(=O)OC

Technology Process of Methoxatin trimethyl ester

There total 1 articles about Methoxatin trimethyl ester 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:

dimethyl (E)-2-oxoglutaconate (38256-25-6) → trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate (74447-88-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) HCl / 1.) CH₂Cl₂, room temp., 12 h; 2.) 12 h, ether

2: 1.) BBr₃; 2.) MeOH, H₂SO₄ (96percent) / 1.) CH₂Cl₂, room temp., 140 h; 2.) reflux, 48 h

3: 93 percent / benzoyl t-butyl nitroxide / methanol; CHCl₃ / 16 h / Ambient temperature

With hydrogenchloride; methanol; benzoyl t-butyl nitroxide; sulfuric acid; boron tribromide; In methanol; chloroform;

DOI:10.1016/S0040-4020(01)87390-7

Reference yield: 100.0%

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate (74447-88-4) → pyrroloquinoline quinone (72909-34-3)

Guidance literature:

With sodium carbonate; In water; at 30 ℃; for 24h;

DOI:10.1246/bcsj.59.1911

Reference yield: 90.0%

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate (74447-88-4) → 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid disodium salt

Guidance literature:

With sodium carbonate; at 25 - 75 ℃; for 16h; Reagent/catalyst; Temperature;

upstream raw materials:

dimethyl (E)-2-oxoglutaconate

Downstream raw materials:

4,5-Dihydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

5-[(4-Nitro-phenyl)-hydrazono]-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

pyrroloquinoline quinone

C₂₄H₁₇N₃O₇

Refernces