Dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate

Base Information

• Chemical Name: Dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate
• CAS No.: 70783-99-2
• Molecular Formula: C13H16F3O4P
• Molecular Weight: 324.237
• DSSTox Substance ID: DTXSID601141182
• Nikkaji Number: J1.356.488D
• Mol file: 70783-99-2.mol

Synonyms:dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate;SCHEMBL11393286;DTXSID601141182;70783-99-2;Phosphonic acid, [2-oxo-4-[3-(trifluoromethyl)phenyl]butyl]-, dimethyl ester

Chemical Property of Dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 324.07383047
• Heavy Atom Count: 21
• Complexity: 389

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(=O)(CC(=O)CCC1=CC(=CC=C1)C(F)(F)F)OC

Technology Process of Dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate

There total 5 articles about Dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate 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: 80.0%

methyl 3-(3-(trifluoromethyl)phenyl)propanoate (294856-02-3) + dimethyl methane phosphonate (756-79-6) → dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate (70783-99-2)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; at 0 ℃;

methyl 3-(3-(trifluoromethyl)phenyl)propanoate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

ethyl 3-(3-trifluoromethylphenyl)-propionate (70311-33-0) + dimethyl methane phosphonate (756-79-6) → dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate (70783-99-2)

Guidance literature:

With n-butyllithium; acetic acid; In tetrahydrofuran; diethyl ether; hexane; water;

Reference yield:

3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4) → dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate (70783-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / 5 percent Pd/C / ethyl acetate

2.1: MeOH

3.1: N-BuLi / tetrahydrofuran / 0 °C

3.2: 80 percent / tetrahydrofuran

With methanol; n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; 1.1: Catalytic hydrogenation / 2.1: Esterification / 3.1: Metallation / 3.2: Condensation;

DOI:10.1016/S0960-894X(00)00273-0

upstream raw materials:

methyl 3-(3-(trifluoromethyl)phenyl)propanoate

dimethyl methane phosphonate

3-(trifluoromethyl)cinnamic acid

3-(3-trifluoromethylphenyl)propanoic acid

Downstream raw materials:

(3aR,4R,5R,6aS)-5-Hydroxy-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

17-(3-trifluoromethylphenyl)-17-trinor prostaglandin F_2α

(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

Refernces

• 1、 -. "Tertiary alcohols". . . Retrieved 2008/06/13.