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US 2006/0079699 A1Published application
Intermediate compounds and methods for synthesizing chemiluminescent dioxetane substrates
OwnerBrooks Edwards, Rouh-Rong Juo +1inventors
InventorsBrooks Edwards, Rouh-Rong Juo, Alison Sparks
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Abstract
Methods for synthesizing 1,2-dioxetane compounds and intermediate compounds useful in the synthesis of these dioxetane compounds are described. The methods and intermediates allow for the efficient production of dioxetane substrates having electron withdrawing groups via a Homer Emmons coupling route.
Claims45
A method of making a 1,2-dioxetane compound having a structure represented by the formula (I):
- wherein R is an alkyl, aryl, aralkyl or cycloalkyl group having 1-20 carbon atoms optionally comprising 1-5 halogen atoms independently selected from the group consisting of F, Cl, Br and I;
- T is a stabilizing group;
- M is an alkali metal;
- and X is an aromatic, light-emitting fluorophore-forming fluorescent chromophore group capable of absorbing energy to form an excited energy state from which it emits optically detectable energy to return to its original energy state;
- the method comprising:
- oxidizing a compound having the formula (II):
- to form a dioxetane intermediate compound represented by the formula (III):
- and;
- reacting the dioxetane intermediate compound (III) with a base to form the 1,2-dioxetane compound (I);
- wherein D is chosen such that the proton alpha to D is acidic and can be deprotonated by a base resulting in beta-elimination of the ethyl-D group as an ethylene-D group thereby leaving an oxyanion or hydroxyl group.
7 more elements
A dioxetane compound having the formula:
- wherein R is an alkyl, aryl, aralkyl or cycloalkyl group having 1-20 carbon atoms optionally comprising 1-5 halogen atoms independently selected from the group consisting of F, Cl, Br and I;
- T is a stabilizing group;
- M is an alkali metal;
- X is an aromatic, light-emitting fluorophore-forming fluorescent chromophore group capable of absorbing energy to form an excited energy state from which it emits optically detectable energy to return to its original energy state and wherein D is chosen such that the proton alpha to D is acidic and can be deprotonated by a base resulting in beta-elimination of the ethyl-D group as an ethylene-D group thereby leaving an oxyanion or hydroxyl group.
1 more element
A compound of the following general formula:
- wherein R is an alkyl, aryl, aralkyl or cycloalkyl group having 1-20 carbon atoms optionally comprising 1-5 halogen atoms independently selected from the group consisting of F, Cl, Br and I;
- T is a stabilizing group;
- and X is an aromatic, light-emitting fluorophore-forming fluorescent chromophore group capable of absorbing energy to form an excited energy state from which it emits optically detectable energy to return to its original energy state, and wherein D is chosen such that the proton alpha to D is acidic and can be deprotonated by a base resulting in beta-elimination of the ethyl-D group as an ethylene-D group thereby leaving an oxyanion or hydroxyl group.
A compound represented by the formula (III):
- wherein R is an alkyl, aryl, aralkyl or cycloalkyl group having 1-20 carbon atoms comprising 1-5 halogen atoms independently selected from the group consisting of F, Cl, Br and I;
- T is a stabilizing group;
- M is an alkali metal;
- and X is an aromatic, light-emitting fluorophore-forming fluorescent chromophore group capable of absorbing energy to form an excited energy state from which it emits optically detectable energy to return to its original energy state, and wherein D is chosen such that the proton alpha to D is acidic and can be deprotonated by a base resulting in beta-elimination of the ethyl-D group as an ethylene-D group thereby leaving an oxyanion or hydroxyl group.
1 more element
A compound represented by the formula (II):
- wherein R is an alkyl, aryl, aralkyl or cycloalkyl group having 1-20 carbon atoms comprising 1-5 halogen atoms independently selected from the group consisting of F, Cl, Br and I;
- T is a stabilizing group;
- M is an alkali metal;
- and X is an aromatic, light-emitting fluorophore-forming fluorescent chromophore group capable of absorbing energy to form an excited energy state from which it emits optically detectable energy to return to its original energy state, and
- wherein D is chosen such that the proton alpha to D is acidic and can be deprotonated by a base resulting in beta-elimination of the ethyl-D group as an ethylene-D group thereby leaving an oxyanion or hydroxyl group.
2 more elements
Dependencies are inferred from the claim text.