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809292

Sigma-Aldrich

3-Methyl-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undecane-2,4-dione

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About This Item

Empirical Formula (Hill Notation):
C15H13F4NO4
CAS Number:
1632145-37-9
Molecular Weight:
347.26
MDL number:
MFCD28359682
UNSPSC Code:
12352200
PubChem Substance ID:
329769153

form

powder or crystals

storage temp.

2-8°C

SMILES string

O=C(C1(C)C2=C(F)C(F)=NC(F)=C2F)OC3(CCCCC3)OC1=O

InChI

1S/C15H13F4NO4/c1-14(7-8(16)10(18)20-11(19)9(7)17)12(21)23-15(24-13(14)22)5-3-2-4-6-15/h2-6H2,1H3

InChI key

PWILGKQKDOVPSH-UHFFFAOYSA-N

General description

3-Methyl-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undecane-2,4-dione is a substituted Meldrum′s acid derivative. It can be prepared by reacting 3-methyl-1,5-dioxaspiro[5.5]undecane-2,4-dione with pentafluoropyridine.

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

Certificates of Analysis (COA)

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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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