2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone

Base Information

• Chemical Name: 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone
• CAS No.: 16691-79-5
• Molecular Formula: C21H16 O5
• Molecular Weight: 348.355
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID90385070
• Nikkaji Number: J524.023I
• Wikidata: Q82177631
• Mol file: 16691-79-5.mol

Synonyms:16691-79-5;2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone;dimethyl 2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate;2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylic acid dimethyl ester;Maybridge3_004625;Oprea1_018179;2,5-bis-(Methoxycarbonyl)-3,4-diphenylcyclopentadienone;SCHEMBL11720920;DTXSID90385070;NTXFYWYVVGMAGT-UHFFFAOYSA-N;HMS1444C05;CCG-51852;MFCD00111095;AKOS024323845;3,5-Cyclopentadiene-1,3-dicarboxylic acid, 2-oxo-4,5-diphenyl-, dimethyl ester;IDI1_016012;Bismethoxycarbonyldiphenylcyclopentadienone;B1962;CS-0447800;FT-0637400;T70394;A810792;SR-01000641128-1;2,5-bis-(carbomethoxy)-3,4-diphenylcyclopentadienone;Dimethyl 3,4-Diphenylcyclopentadienone-2,5-dicarboxylate;3,4-Diphenylcyclopentadienone-2,5-dicarboxylic Acid Dimethyl Ester;2-OXO-4,5-DIPHENYL-CYCLOPENTA-3,5-DIENE-1,3-DICARBOXYLIC ACID DIMETHYL ESTER;dimethyl 2-oxidanylidene-4,5-diphenyl-cyclopenta-3,5-diene-1,3-dicarboxylate

Chemical Property of 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone

Chemical Property:

• Vapor Pressure: 3.96E-08mmHg at 25°C
• Melting Point: 175 °C
• Refractive Index: 1.613
• Boiling Point: 445.4°C at 760 mmHg
• Flash Point: 194.3°C
• PSA: 69.67000
• Density: 1.302g/cm³
• LogP: 2.82270
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 348.09977361
• Heavy Atom Count: 26
• Complexity: 602

Purity/Quality:

97% ^*data from raw suppliers

2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C(=C(C1=O)C(=O)OC)C2=CC=CC=C2)C3=CC=CC=C3
• Recent ClinicalTrials: A Study of B1962, a PD-L1/VEGF Bispecific Antibody Fusion Protein, for Advanced Solid Tumors

Technology Process of 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone

There total 8 articles about 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone 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: 99.6%

2,5-dimethoxycarbonyl-4-hydroxy-3,4-diphenylcyclopentene-2-one (16691-78-4) → 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (16691-79-5)

Guidance literature:

With acetic anhydride;

Reference yield: 96.0%

3-oxopentanedioic acid dimethyl ester (1830-54-2) + benzil (134-81-6) → 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (16691-79-5)

Guidance literature:

3-oxopentanedioic acid dimethyl ester; benzil; With potassium hydroxide; In ethanol;

With acetic anhydride; In acetic acid;

DOI:10.1055/s-2005-863727

Reference yield:

3-oxopentanedioic acid dimethyl ester (1830-54-2) → 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (16691-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol

2: TsOH / benzene

With toluene-4-sulfonic acid; In methanol; benzene;

DOI:10.1039/j39670001986

upstream raw materials:

2,5-dimethoxycarbonyl-4-hydroxy-3,4-diphenylcyclopentene-2-one

5-Hydroxy-2-methoxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester

3-oxopentanedioic acid dimethyl ester

benzil

Downstream raw materials:

4-oxo-6,6a-diphenyl-3-p-tolyl-(6ac)-4,6a-dihydro-cyclopenta[d]isoxazol-3ar,5-dicarboxylic acid dimethyl ester

(1S,4R,5S)-5-(4-Chloro-phenyl)-7-oxo-2,3-diphenyl-bicyclo[2.2.1]hept-2-ene-1,4-dicarboxylic acid dimethyl ester

(1S,4R,5R)-5-(4-Chloro-phenyl)-7-oxo-2,3-diphenyl-bicyclo[2.2.1]hept-2-ene-1,4-dicarboxylic acid dimethyl ester

(Z)-(1S,4R,4aR,10aS)-11-Oxo-2,3-diphenyl-4a,5,6,9,10,10a-hexahydro-1,4-methano-benzocyclooctene-1,4-dicarboxylic acid dimethyl ester