809160

N-Ethyl-N-isopropylpropan-2-aminium 3-(4-Acetyl-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate

• Empirical Formula (Hill Notation): C₂₅H₃₃F₄NO₅
• CAS Number: 1632145-26-6
• Molecular Weight: 503.53
• UNSPSC Code: 12352200
• PubChem Substance ID: 329769143
• NACRES: NA.22
• Form: powder

Properties

• form: powder
• storage temp.: 2-8°C
• SMILES string: FC1=C(C(C)=O)C(F)=C(F)C(C2=C([O-])OC3(CCCCC3)OC2=O)=C1F.CC[NH+](C(C)C)C(C)C
• InChI: 1S/C17H14F4O5.C8H19N/c1-7(22)8-11(18)13(20)9(14(21)12(8)19)10-15(23)25-17(26-16(10)24)5-3-2-4-6-17;1-6-9(7(2)3)8(4)5/h23H,2-6H2,1H3;7-8H,6H2,1-5H3
• InChI key: UYTIIFFVFGALQP-UHFFFAOYSA-N

Description

General description

N-Ethyl-N-isopropylpropan-2-aminium 3-(4-acetyl-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate is a fluoroarylated-Meldrum′s acid adduct. It can be prepared by reacting 2′,3′,4′,5′,6′-pentafluoroacetophenone with cyclohexyl-Meldrum′s acid in the presence of N,N-diisopropylethylamine and acetonitrile.

Application

This compound undergoes cycloreversion to form the fluoro(hetero)aryl ketene, which undergoes efficient coupling with nucleophiles and allows rapid incorporation of highly fluorinated α-fluoro(hetero)aryl acetic acid derivatives.

Other Notes

Selective Perfluoro- and Polyfluoroarylation of Meldrum′s Acid