1-(4-Methoxyphenyl)-3-phenyl-1,2-propanedione

Base Information

• Chemical Name: 1-(4-Methoxyphenyl)-3-phenyl-1,2-propanedione
• CAS No.: 150881-78-0
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.285
• DSSTox Substance ID: DTXSID301251069
• Mol file: 150881-78-0.mol

Synonyms:DTXSID301251069;1-(4-Methoxyphenyl)-3-phenyl-1,2-propanedione;150881-78-0

Chemical Property of 1-(4-Methoxyphenyl)-3-phenyl-1,2-propanedione

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 254.094294304
• Heavy Atom Count: 19
• Complexity: 310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(=O)C(=O)CC2=CC=CC=C2

Technology Process of 1-(4-Methoxyphenyl)-3-phenyl-1,2-propanedione

There total 11 articles about 1-(4-Methoxyphenyl)-3-phenyl-1,2-propanedione 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: 96.0%

1-(p-methoxyphenyl)-3-phenyl-2,3-epoxy-1-propanone (40327-51-3) → 1-(4-methoxyphenyl)-3-phenylpropane-1,2-dione (150881-78-0)

Guidance literature:

With silica gel; In hexane; dichloromethane; for 24h;

DOI:10.1080/00397919308011247

Reference yield: 58.0%

methyl 2-oxo-2-phenylacetate (15206-55-0) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → 1-(4-methoxyphenyl)-3-phenylpropane-1,2-dione (150881-78-0)

Guidance literature:

methyl 2-oxo-2-phenylacetate; 2-Bromo-4'-methoxyacetophenone; With potassium carbonate; In 1-methyl-pyrrolidin-2-one; methanol; at 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; methanol; water; at 20 ℃; for 2h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.6b02575

Reference yield:

C24H23NO2S → α-hydroxy-4'-methoxy-chalcone (59648-53-2) + 1-(4-methoxyphenyl)-3-phenylpropane-1,2-dione (150881-78-0)

Guidance literature:

With silver tetrafluoroborate; water; In acetonitrile; at 60 ℃; for 2h; Overall yield = 68 percent; Overall yield = 18 mg; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04109

upstream raw materials:

α-hydroxy-4'-methoxy-chalcone

4,α-dimethoxy-chalcone

3-chloro-2-hydroxy-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one

sodium ethanolate

Downstream raw materials:

2-hydroxy-2-(4-methoxy-phenyl)-3-phenyl-propionic acid

α-hydroxy-4'-methoxy-chalcone

2-benzyl-3-(4-methoxy-phenyl)-quinoxaline

Refernces

• 1、 He, Zhen,Qi, Xiaotian,She, Zhijie,Zhao, Yinsong,Li, Shiqing,Tang, Junbin,Gao, Ge,Lan, Yu,You, Jingsong. "Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones". supporting information. p. 1403 - 1411. Retrieved 2017/02/10.