alpha-Fluoro-alpha-methyl-beta-oxo-benzenepropanoic acid methyl ester

Base Information

• Chemical Name: alpha-Fluoro-alpha-methyl-beta-oxo-benzenepropanoic acid methyl ester
• CAS No.: 765271-39-4
• Molecular Formula: C₁₁H₁₁FO₃
• Molecular Weight: 210.205
• DSSTox Substance ID: DTXSID50470719
• Mol file: 765271-39-4.mol

Synonyms:765271-39-4;ALPHA-FLUORO-ALPHA-METHYL-BETA-OXO-BENZENEPROPANOIC ACID METHYL ESTER;DTXSID50470719;Benzenepropanoic acid,alpha-fluoro-alpha-methyl-beta-oxo-,methyl ester(9ci)

Chemical Property of alpha-Fluoro-alpha-methyl-beta-oxo-benzenepropanoic acid methyl ester

Chemical Property:

• PSA: 43.37000
• LogP: 1.77050
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 210.06922237
• Heavy Atom Count: 15
• Complexity: 259

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of alpha-Fluoro-alpha-methyl-beta-oxo-benzenepropanoic acid methyl ester

There total 14 articles about alpha-Fluoro-alpha-methyl-beta-oxo-benzenepropanoic acid methyl ester 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: 67.0%

methyl 2-benzoylpropionate (32742-19-1,116782-25-3,29540-54-3) → methyl 2-fluoro-2-methyl-3-oxo-3-phenylpropionate (765271-39-4)

Guidance literature:

With titanium(IV) isopropylate; N-fluorobis(methanesulfonyl)imide; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c5gc02612a

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + tert-butyl 2-benzoylpropionate (104015-38-5) → (R)-methyl 2-fluoro-2-methyl-3-oxo-3-phenyl-propionate (144462-33-9,765271-39-4)

Guidance literature:

tert-butyl 2-benzoylpropionate; With N-fluorobis(benzenesulfon)imide; In ethanol; at 20 ℃; for 40h;

With trifluoroacetic acid; at 20 ℃; for 2h;

diazomethane; In diethyl ether; Further stages.;

DOI:10.1021/ja028464f

Reference yield:

tert-butyl 2-benzoylpropionate (104015-38-5) → (R)-methyl 2-fluoro-2-methyl-3-oxo-3-phenyl-propionate (144462-33-9,765271-39-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N-fluorobenzenesulfonimide / chiral palladium complex / ethanol / 48 h / 20 °C

2: trifluoroacetic acid

With N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; chiral palladium complex; In ethanol;

DOI:10.1016/j.tet.2005.12.070

upstream raw materials:

diazomethane

methanol

(3S,4S,6R,7S,10R)-3,4-Difluoro-7-isopropyl-3,10-dimethyl-4-phenyl-1,5-dioxa-spiro[5.5]undecan-2-one

methyl 2-benzoylpropionate

Refernces

• 1、 Fukushi, Kazunobu,Suzuki, Satoru,Kamo, Tomohiro,Tokunaga, Etsuko,Sumii, Yuji,Kagawa, Takumi,Kawada, Kosuke,Shibata, Norio. "Methyl NFSI: Atom-economical alternative to NFSI shows higher fluorination reactivity under Lewis acid-catalysis and non-catalysis". supporting information. p. 1864 - 1868. Retrieved 2016/04/19.
• 2、 Hamashima, Yoshitaka,Suzuki, Toshiaki,Takano, Hisashi,Shimura, Yuta,Tsuchiya, Yasunori,Moriya, Ken-ichi,Goto, Tomomi,Sodeoka, Mikiko. "Highly enantioselective fluorination reactions of β-ketoesters and β-ketophosphonates catalyzed by chiral palladium complexes". . p. 7168 - 7179. Retrieved 2007/10/03.