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Chemiluminescent 1,2-dioxietanes

A dioxetane and single-ring technology, which is applied in the field of chemiluminescence 1,2-dioxetane with a power supply on the four-membered peroxide ring, can solve the problems of poor luminescence and the like

Inactive Publication Date: 2001-12-05
布里奇 P 吉利
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] While these existing compounds provide enzymatically cleavable 1,2-dioxetanes, it has been observed that these molecules are particularly poorly luminescent in aqueous buffers, especially when trace amounts of biological substances need to be detected

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0081] This example illustrates that [(4-methoxy)-4-(3-phosphoryloxyphenyl)spiro[1,2-dioxetane-3,2′-adamantane-4,5-ene] Preparation method of disodium salt (46). The reaction sequence is as follows:

[0082] (a) Synthesis of 5-hydroxyadamantan-2-one (40)

[0083] In a single necked 500 mL round bottom flask equipped with a magnetic stirrer and water bath was added 75 parts of acetic acid containing 5 parts of acetic anhydride. 25 parts of chromium trioxide were added in portions over 40 minutes while maintaining the temperature at 15-20°C with a water bath. Add 5 parts of adamantan-2-one in portions over 15 minutes. Stirring was continued for 1 hour. The viscous reaction mixture was poured into cold 250 mL of 20% aqueous sodium hydroxide. The aqueous layer was extracted three times with 250 ml of ethyl acetate, and washed twice with 250 ml of water. Then dry over sodium sulfate. The solvent was distilled off under reduced pressure and chromatographed on a silica gel col...

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PUM

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Abstract

Chemiluminescent 1,2-dioxetanes derived from substituted aromatic esters or ketones and spiro-fused ketones with either pi -electron system in the ring or with carbon-carbon double bond or triple bond(s) in the spiro-fused ring are provided herein. These 1,2-dioxetanes have electron donating or withdrawing groups at the four-membered peroxide ring, thus, the 1,2-dioxetanes ring hereof is affected by the added electronic charge.

Description

[0001] This application is a completed application of pending US Provisional Patent Application 60 / 099693, filed September 8, 1998, entitled "Chemiluminescent 1,2-dioxetanes." The entire content of this application is incorporated herein by reference. Background of the invention [0002] 1. field of invention [0003] The present invention relates to chemiluminescent compounds. In particular, the present invention relates to stable, triggerable chemiluminescent 1,2-dioxetanes. More specifically, the present invention relates to novel chemiluminescent 1,2-dioxetane compounds prepared by oxidation of novel alkenes. The above alkenes are prepared by coupling substituted aromatic esters or ketones with spiro-fused ketones with or without a π-electron system or carbon-carbon double bond in the ring. [0004] 2. current technology [0005] Chemiluminescent compounds and their production and use have long been described in the prior art literature. These "high-energy" molecule...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/12C07F9/655
CPCC07F9/12C07F9/65512
Inventor 布里奇·P·吉利
Owner 布里奇 P 吉利