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Sigma-Aldrich

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

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About This Item

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

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

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

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Sameera M Senaweera et al.
The Journal of organic chemistry, 79(21), 10466-10476 (2014-10-02)
This work describes the facile and mono-selective per- and polyfluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated α-phenyl acetic acid derivatives, which provide straightforward access to fluorinated building blocks. The reaction takes place quickly, and most

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