Methyl 2,5-diphenylfuran-3-carboxylate

Base Information

• Chemical Name: Methyl 2,5-diphenylfuran-3-carboxylate
• CAS No.: 84302-12-5
• Molecular Formula: C18H14O3
• Molecular Weight: 278.307
• DSSTox Substance ID: DTXSID40574735
• Nikkaji Number: J1.919.760C
• Wikidata: Q82463886

Synonyms:Methyl 2,5-diphenylfuran-3-carboxylate;84302-12-5;DTXSID40574735

Chemical Property of Methyl 2,5-diphenylfuran-3-carboxylate

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 278.094294304
• Heavy Atom Count: 21
• Complexity: 342

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(OC(=C1)C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of Methyl 2,5-diphenylfuran-3-carboxylate

There total 11 articles about Methyl 2,5-diphenylfuran-3-carboxylate 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: 85.0%

methanol (67-56-1) + 1,5-diphenyl-2,4-pentadiyn-1-one (1574-79-4) → methyl 2,5-diphenylfuran-3-carboxylate (84302-12-5)

Guidance literature:

With silver hexafluoroantimonate; 3,5-dicholoropyridine N-oxide; chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); In 1,2-dichloro-ethane; at 80 ℃; for 2h; regioselective reaction; Glovebox; Sealed tube; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02389

Reference yield: 57.0%

(1R,4R)-1,4-Diphenyl-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene-5-carboxylic acid methyl ester (84302-19-2) → methyl 2,5-diphenylfuran-3-carboxylate (84302-12-5) + (2R,3S)-2,3-Dibenzoyl-oxirane-2-carboxylic acid methyl ester (88073-33-0,90043-58-6) + Benzoic acid (Z)-1-methoxycarbonyl-3-oxo-3-phenyl-propenyl ester (84302-13-6) + Benzoic acid (E)-2-methoxycarbonyl-3-oxo-3-phenyl-propenyl ester

Guidance literature:

In tetrachloromethane; at 4 ℃; Further byproducts given. Yields of byproduct given;

Reference yield: 47.0%

methyl 2-methoxy-5-phenyl-furan-3-carboxylate (115852-13-6) + phenylmagnesium bromide → methyl 2,5-diphenylfuran-3-carboxylate (84302-12-5)

Guidance literature:

In diethyl ether; at 20 ℃;

DOI:10.1016/S0040-4039(03)01430-8

upstream raw materials:

(E)-2-Benzoyl-4-oxo-4-phenyl-but-2-enoic acid methyl ester

(1R,4R)-1,4-Diphenyl-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene-5-carboxylic acid methyl ester

methyl α,β-dibenzoyl-propionate

methanol

Downstream raw materials:

(E)-2-Benzoyl-4-oxo-4-phenyl-but-2-enoic acid methyl ester

(3R,3aR,6aS)-2-Oxo-5,6a-diphenyl-2,3,3a,6a-tetrahydro-furo[2,3-b]furan-3,4-dicarboxylic acid dimethyl ester

Benzoic acid (Z)-1-methoxycarbonyl-3-oxo-3-phenyl-propenyl ester

(1R,4R)-1,4-Diphenyl-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene-5-carboxylic acid methyl ester

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