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809225

Sigma-Aldrich

N-Ethyl-N-isopropylpropan-2-aminium 4-Oxo-3-(2,3,5,6-tetrafluoro-4-(methoxycarbonyl)phenyl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate

≥95%

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About This Item

Empirical Formula (Hill Notation):
C25H33F4NO6
CAS Number:
1632145-20-0
Molecular Weight:
519.53
UNSPSC Code:
12352200
PubChem Substance ID:
329769149
NACRES:
NA.22

assay

≥95%

form

powder

mp

117-122 °C

storage temp.

2-8°C

SMILES string

FC1=C(C(OC)=O)C(F)=C(F)C(C2=C([O-])OC3(CCCCC3)OC2=O)=C1F.CC[NH+](C(C)C)C(C)C

InChI

1S/C17H14F4O6.C8H19N/c1-25-14(22)9-12(20)10(18)7(11(19)13(9)21)8-15(23)26-17(27-16(8)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

CJYWUHPRPZRMSC-UHFFFAOYSA-N

General description

N-Ethyl-N-isopropylpropan-2-aminium 4-oxo-3-(2,3,5,6-tetrafluoro-4-(methoxycarbonyl)phenyl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate is a fluoroarylated-Meldrum′s acid adduct. It can be prepared by reacting methyl-2,3,4,5,6-pentafluorobenzoate with cyclohexyl Meldrum′s acid.[1]

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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