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Merck
CN

809195

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:
Molecular Weight:
375.31
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
Form:
powder
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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.


Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Related Content

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.


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



Global Trade Item Number

SKUGTIN
809195-250MG04061833243992