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Sigma-Aldrich

N-Ethyl-N-isopropylpropan-2-aminium 3-(4-Acetyl-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate

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About This Item

Empirische Formel (Hill-System):
C25H33F4NO5
CAS-Nummer:
1632145-26-6
Molekulargewicht:
503.53
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329769143
NACRES:
NA.22

Form

powder

Lagertemp.

2-8°C

SMILES String

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

InChI

1S/C17H14F4O5.C8H19N/c1-7(22)8-11(18)13(20)9(14(21)12(8)19)10-15(23)25-17(26-16(10)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

InChIKey

UYTIIFFVFGALQP-UHFFFAOYSA-N

Allgemeine Beschreibung

N-Ethyl-N-isopropylpropan-2-aminium 3-(4-acetyl-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate is a fluoroarylated-Meldrum′s acid adduct. It can be prepared by reacting 2′,3′,4′,5′,6′-pentafluoroacetophenone with cyclohexyl-Meldrum′s acid in the presence of N,N-diisopropylethylamine and acetonitrile.

Anwendung

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.

Sonstige Hinweise

Selective Perfluoro- and Polyfluoroarylation of Meldrum′s Acid

Analysenzertifikate (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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Weaver Group – Professor Product Portal

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.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

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