134519-01-0Relevant articles and documents
Comparison of convenient alternative synthetic approaches to 4-[(3-tert-butyldimethylsilyloxy)phenyl]-4-methoxyspiro[1,2-dioxetane-3, 2′-adamantane]
Bastos, Erick Leite,Leite Ciscato, Luiz Francisco Monteiro,Weiss, Dieter,Beckert, Rainer,Baader, Wilhelm Josef
, p. 1781 - 1786 (2006)
The preparation of 4-(3-tert-butyldimethylsilyloxyphenyl)-4-methoxyspiro[1, 2-dioxetane-3,2′-adamantane] by two different approaches is described and the results are compared with previously reported data. The precursor olefin, 1-[3-(tert-butyldimethylsilyloxy)phenyl]-1-methoxy-2-spiroadamantylidene is obtained from 3-hydroxybenzaldehyde by both Horner-Wadsworth-Emmons and McMurry coupling reactions in 42% overall yield in both cases. 1,2-Dioxetane preparation by singlet oxygen addition, obtained through calcium peroxide diperoxohydrate thermolysis, is compared with conventional photooxygenation. Georg Thieme Verlag Stuttgart.
Chemiluminescent 3-(substituted Adamant-2'-Ylidene) 1,2-dioxetanes
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, (2008/06/13)
Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: STR1 The corresponding dioxetanes which, instead of being substituted at the 5' or 7', or at the 5' and 7' positions, instead contain a 4' methylene group, are also disclosed, as are intermediates for all these 3-substituted adamant-2'-ylidenedioxetanes, and their use as reporter molecules in assays.
Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes
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, (2008/06/13)
Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: STR1 wherein: X and X1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X1 being other than hydrogen; and R1 and R2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R1 and R2 represent individual substituents the R2 substituent is aromatic, heteroaromatic, or an unsaturated substituent in conjugation with an aromatic ring, and that at least one of R1 and R2 is, or R1 and R2 taken together are, an enzymatically cleavable labile group-substituted fluorescent chromophore group that produces a luminescent substance when the enzymatically cleavable labile substituent thereof is removed by an enzyme. The corresponding dioxetanes which, instead of being substituted at the 5' or 7', or at the 5' and 7' positions, instead contain a 4' methylene group, are also disclosed, as are intermediates for all these 3-substituted adamant-2'-ylidenedioxetanes, and their use as reporter molecules in assays.