Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

Base Information

• Chemical Name: Ethyl 4-(4-fluorophenyl)-3-oxobutanoate
• CAS No.: 221121-37-5
• Molecular Formula: C12H13FO3
• Molecular Weight: 224.232
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID60442109
• Wikidata: Q82259204
• Mol file: 221121-37-5.mol

Synonyms:221121-37-5;ethyl 4-(4-fluorophenyl)-3-oxobutanoate;4-(4-Fluoro-phenyl)-3-oxo-butyric acid ethyl ester;SCHEMBL699965;4-(4-FLUORO-PHENYL)-3-OXO-BUTYRICACIDETHYLESTER;DTXSID60442109;Ethyl 4-fluorophenylacethylacetate;QCQKQRINQDBSEZ-UHFFFAOYSA-N;MFCD03844416;AKOS010951792;AT28332;ethyl4-(4-fluorophenyl)-3-oxobutanoate;FT-0754799;4-(4-fluorophenyl)-3-oxobutanoic acid ethyl ester;A1-00560;F2136-0001

Chemical Property of Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.493
• Boiling Point: 295.509 °C at 760 mmHg
• PKA: 10.35±0.46(Predicted)
• Flash Point: 128.353 °C
• PSA: 43.37000
• Density: 1.161 g/cm³
• LogP: 1.89050
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 224.08487243
• Heavy Atom Count: 16
• Complexity: 245

Purity/Quality:

99%min ^*data from raw suppliers

Ethyl4-(4-Fluorophenyl)-3-oxobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)CC1=CC=C(C=C1)F
• Uses: Ethyl 4-(4-Fluorophenyl)-3-oxobutanoate is used in the synthesis of novel pyridinone derivatives as non-nucleoside reverse transcriptase inhibitors with high potency against NNRTI-resistant HIV-1 strains. Also used in the structural evaluation of 2-substituted 5-hydroxyindole 3-carboxylates as potent inhibitors of human 5-lipoxygenase.

Technology Process of Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

There total 12 articles about Ethyl 4-(4-fluorophenyl)-3-oxobutanoate 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: 98.0%

diazoacetic acid ethyl ester (623-73-4) + 4-fluorostyrene oxide (18511-62-1,53631-23-5,134356-73-3,134356-74-4) → 4-(4-fluorophenyl)-3-oxobutanoic acid ethyl ester (221121-37-5)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at 20 ℃; for 0.5h;

Reference yield: 87.0%

cycl-isopropylidene malonate (2033-24-1) + ethanol (64-17-5) + 4-Fluorophenylacetyl chloride (459-04-1) → 4-(4-fluorophenyl)-3-oxobutanoic acid ethyl ester (221121-37-5)

Guidance literature:

cycl-isopropylidene malonate; 4-Fluorophenylacetyl chloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 4h;

ethanol; for 2h; Heating;

DOI:10.1021/ja060729t

Reference yield: 86.8%

cycl-isopropylidene malonate (2033-24-1) + 4-Fluorophenylacetyl chloride (459-04-1) → 4-(4-fluorophenyl)-3-oxobutanoic acid ethyl ester (221121-37-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

upstream raw materials:

ethyl potassium malonate

2-(4-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one

cycl-isopropylidene malonate

ethanol

Downstream raw materials:

6-(4-fluoro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

7-amino-4-(4-fluoro-benzyl)-1H-quinolin-2-one

ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

6-(4-fluorobenzyl)-7H-benzo[f]pyrido[1,2-b][2,7]naphthyridin-7-one

Refernces

• 1、 -. "PYRIDONE COMPOUNDS AND METHODS OF USE IN THE MODULATION OF A PROTEIN KINASE". Paragraph 0263. . Retrieved 2021/04/02.
• 2、 -. "Novel quinoline derivative inhibitor". . . Retrieved 2020/03/12.