Cyclopropenones and the photochemical generation of cyclic alkynes therefrom
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorsVladimir V. Popik, Andrei A. Poloukhtine, Geert-Jan Boons, Margaretha Wolfert
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Abstract
Cyclic alkynes (e.g., cyclooctynes such as dibenzocyclooctynes) can be photochemically generated from cyclopropenones as disclosed herein. The cyclic alkynes can be reacted (e.g., in situ) with materials having alkyne-reactive groups (e.g., azide groups in a “click” reaction). In preferred embodiments, the generation and reaction of the cyclic alkyne can proceed in the absence of a catalyst (e.g., Cu(I)). These reactions can be useful, for example, for the selective labeling of living cells that are metabolically modified with azido-containing surface monosaccharides, or for light-directed surface patterning.
Claims44
A compound having the formula:
- wherein each Ar is a phenyl group;
- E represents C(R4)2;
- and each R4 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, a C1-C10 organic group, and a linking group;
- wherein at least one Ar is a phenyl group in which one or more carbon atoms of the phenyl group are substituted with a substituent selected from the group consisting of alkyl, aryl, heteroaryl, halogen, nitro, cyano, hydroxyl, alkoxyl, aryloxyl;
- thio, mercapto, alkylthio, arylthio, amino, alkylamino, arylamino, dialkylamino, diarylamino, arylalkylamino, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, arylalkylaminocarbonyl, carboxyl, alkyloxycarbonyl, aryloxycarbonyl, aldehyde, arylcarbonyl, alkylcarbonyl, iminyl, aryliminyl, alkyliminyl, sulfo, alkylsulfonyl, arylsulfonyl, hydroximinyl, aryloximinyl, and alkoximinyl;
- and
- wherein two or more alkyl or heteroalkyl substituents of a phenyl group may optionally be combined to form fused aryl-alkyl or aryl-heteroalkyl ring systems.
A compound having the formula:
- wherein each Ar is a phenyl group;
- G represents CR6;
- and each R5 and R6 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, a C1-C10 organic group, and a linking group.
A compound having the formula I:
- wherein:
- R1 is selected from the group consisting of:
- an alkoxy and a hydroxyl;
- R2 is selected from the group consisting of:
- an alkyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an aryl, an alkoxy, a carboxy, a hydroxyl, an ether, an ester, and a halogen;
- and
- the cyclooctyne is a dibenzocyclooctyne.
Dependencies are inferred from the claim text.