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809195

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C17H17F4NO4
CAS Number:
1632145-38-0
Molecular Weight:
375.31
MDL number:
MFCD28359683
UNSPSC Code:
12352200
PubChem Substance ID:
329769146

form

powder

storage temp.

2-8°C

SMILES string

FC1=C(F)N=C(F)C(F)=C1C2(CCC)C(OC3(CCCCC3)OC2=O)=O

InChI

1S/C17H17F4NO4/c1-2-6-17(9-10(18)12(20)22-13(21)11(9)19)14(23)25-16(26-15(17)24)7-4-3-5-8-16/h2-8H2,1H3

InChI key

OJBHZVGQJBBEDE-UHFFFAOYSA-N

General description

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

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

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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