189626-04-8

Basic information

• Product Name: 2,3-Butadienoic acid, 4-(4-fluorophenyl)-2-methyl-, ethyl ester
• CAS NO: 189626-04-8
• Molecular Formula: C13H13FO2
• Molecular Weight: 220.243
• Mol File: 189626-04-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,3-Butadienoic acid, 4-(4-fluorophenyl)-2-methyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Butadienoic acid, 4-(4-fluorophenyl)-2-methyl-, ethyl ester(189626-04-8)
• EPA Substance Registry System: 2,3-Butadienoic acid, 4-(4-fluorophenyl)-2-methyl-, ethyl ester(189626-04-8)

Safety Data

• Hazardous Substances Data: 189626-04-8(Hazardous Substances Data)

Upstream product

• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 30018-16-7 (1-ethoxycarbonylethyl)triphenylphosphonium bromide 

Downstream Products

• 1089678-71-6 4-allyl-1-(4'-fluorophenyl)-3-methyl-1,2,6-heptatrien-4-ol 
• 1042096-66-1 ethyl 2-acetyl-2,3-dimethyl-4-(4'-fluorophenyl)-3(E)-butenoate 
• 1042096-79-6 ethyl 2-(1'-(4''-fluorophenyl)-1'(Z)-propen-2'-yl)-2-methyl-4-pentenoate 
• 1042096-96-7 ethyl 2-(1'-(4''-fluorophenyl)-1'(E)-propen-2'-yl)-2-methyl-4-pentenoate 
• 1042096-51-4 ethyl 2-acetyl-2,3-dimethyl-4-(4'-fluorophenyl)-3(Z)-butenoate 
• 1206896-53-8 ethyl 3-fluoro-4-(4'-fluorophenyl)-2-methyl-4-oxo-2(E)-butenoate 
• 1206896-61-8 4-fluoro-5-(4'-fluorophenyl)-3-methyl-2(5H)-furanone 
• 1227259-18-8 2-ethoxycarbonyl-3-[1-(4-fluorophenyl)meth-(E)-ylidene]-4-methylpentanedioic acid 1-tert-butyl ester 5-ethyl ester 
• 1227751-54-3 ethyl 4-(4-fluorophenyl)-2-methyl-4-(2,4,6-trimethoxyphenyl)but-2(E)-enoate 
• 1227751-59-8 ethyl 4-(4-fluorophenyl)-4-(4-methoxyphenyl)-2-methylbut-2(E)-enoate 
• 1380396-89-3 ethyl (2E)-5-acetyl-4-(4-fluorophenyl)-2-methyl-6-oxohept-2-enoate 
• 1380397-04-5 4-acetyl-3-[2-(4-fluorophenyl)-2-oxoethyl]-3,5-dimethylfuran-2(3H)-one 
• 1227259-20-2 3-[1-(4-fluorophenyl)meth-(Z)-ylidene]-2-methylpentanedioic acid 5-tert-butyl ester 
• 1280135-84-3 ethyl 2-methyl-4-(4-fluorophenyl)-4-(1-tosyl-1H-indol-3-yl)but-2(Z)-enoate 

Relevant articles and documents

An efficient large-scale synthesis of a naphthylacetic acid CRTH2 receptor antagonist

An efficient and practical synthesis of a naphthylacetic acid CRTH2 receptor antagonist is reported. Michael addition of ethyl t-butyl malonate to an allenoate afforded a triester, which was selectively hydrolyzed and decarboxylated to give a benzylidenepentanedioic acid monoester. Treatment of this compound with potassium acetate and acetic anhydride produced the naphthylacetate core. The triflate of the key building block was coupled with a zinc reagent of the side chain under improved Negishi coupling conditions to afford the target product. The process was successfully scaled up to produce over 2 kg of the API.

NAPHTHYLACETIC ACIDS

The invention is concerned with the compounds of formula (I) and pharmaceutically acceptable salts and esters thereof, wherein X, Q, and R1-R6 are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds of formula (I) are antagonists or partial agonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: An efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates

Different from the reaction of 2,3-allenoic acids with Selectfluor, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor under different conditions in moderate yields. The reaction of 2, 4, 4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed. The Royal Society of Chemistry 2010.