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809160

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

Name: <I>N</I>-Ethyl-<I>N</I>-isopropylpropan-2-aminium 3-(4-Acetyl-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate
Brand: ALDRICH

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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):

C₂₅H₃₃F₄NO₅

Numer CAS:

1632145-26-6

Masa cząsteczkowa:

503.53

UNSPSC Code:

12352200

PubChem Substance ID:

329769143

NACRES:

NA.22

Form:

powder

Pomoc techniczna

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Właściwości

form

powder

storage temp.

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

InChI key

UYTIIFFVFGALQP-UHFFFAOYSA-N

Opis

General description

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.

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

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Powiązane treści

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.

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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809160-1G	04061826647868