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809209

4-(2,4-Dioxo-3-propyl-1,5-dioxaspiro[5.5]-undecan-3-yl)-2,3,5,6-tetrafluorobenzonitrile

Name: 4-(2,4-Dioxo-3-propyl-1,5-dioxaspiro[5.5]-undecan-3-yl)-2,3,5,6-tetrafluorobenzonitrile
Brand: ALDRICH

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About This Item

Fórmula empírica (notación de Hill):

C₁₉H₁₇F₄NO₄

Número de CAS:

1632145-41-5

Peso molecular:

399.34

MDL number:

MFCD28359685

UNSPSC Code:

12352200

PubChem Substance ID:

329769147

NACRES:

NA.22

form

powder

storage temp.

2-8°C

SMILES string

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

InChI

1S/C19H17F4NO4/c1-2-6-19(11-14(22)12(20)10(9-24)13(21)15(11)23)16(25)27-18(28-17(19)26)7-4-3-5-8-18/h2-8H2,1H3

InChI key

YAKREKYYFSATAN-UHFFFAOYSA-N

General description

4-(2,4-Dioxo-3-propyl-1,5-dioxaspiro[5.5]-undecan-3-yl)-2,3,5,6-tetrafluorobenzonitrile is a substituted Meldrum′s acid derivative. It can be prepared by reacting pentafluorobenzonitrile 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

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Selective perfluoro- and polyfluoroarylation of Meldrum's acid.

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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Organofluorine chemistry is an essential part of drug discovery programs as well as agrochemical programs and even plays a major role in materials chemistry. Despite the undeniable importance of fluorinated organic molecules, our ability to synthesize these substrates is lacking - though arguably it is better than that of Nature. Consequently, methods that allow facile access to fluorinated molecules are important especially when they provide unique access to fluorinated chemical space.

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