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Synthetic method of 1,2-dioxetane compound

A technology of dioxetane and synthesis method, which is applied in the field of synthesis of chemiluminescent agents, can solve the problems of production danger, many steps, complicated operation, etc., and achieve avoiding the danger of explosion, mild reaction conditions, and good luminescent performance Effect

Active Publication Date: 2015-04-01
广东派特埃尔生物科技有限公司
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AI Technical Summary

Problems solved by technology

The overall yields of these methods are all low; in addition, the preparation of intermediates requires multi-step reactions, separation and purification are relatively difficult and the cost is high; Grignard reagents and photooxidation are used in the process, the operation is complicated, the production is dangerous, and it is difficult to realize larger scale production
[0003] Therefore, the prior art generally has the disadvantages of long synthetic route, many steps, low yield, high cost, complicated operation, and difficulty in large-scale production.

Method used

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  • Synthetic method of 1,2-dioxetane compound
  • Synthetic method of 1,2-dioxetane compound
  • Synthetic method of 1,2-dioxetane compound

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Embodiment 1

[0023] Embodiment one Synthesis of 3-(2′-spiroadamantane)-4-methoxy-4-(3″-phosphoryloxy)benzene-1,2-dioxetane, AMPPD.

[0024] The first step: the preparation of carboxylic acid compound II. 13.81g (100mmol) m-hydroxybenzoic acid, namely Dissolve in 300mL dichloromethane, cool to 0°C, add 54.97g (200mmol) tert-butyldiphenylchlorosilane and 13.62g (200mmol) imidazole successively, stir magnetically, and react at room temperature for 10h. Add 100mL saturated ammonium chloride solution after the monitoring reaction finishes, separate liquids and get the organic phase, this organic phase and the aqueous phase are extracted with 300mL ethyl acetate, and the organic phase obtained by liquid separation is combined, and the solvent is removed by distillation under reduced pressure with a rotary evaporator. Purify the product through the column to obtain 34.64g (92mmo) yellow oil, which is carboxylic acid compound II, namely .

[0025] The second step: the preparation of ester c...

Embodiment 2

[0032] Embodiment two 3-(2′-(5′-chloro)spiroadamantane)-4-methoxy-4-(3″-phosphoryloxy-4″-chloro)benzene-1,2-dioxetane Alkane, that is, the synthesis of CDP-Star.

[0033] The first step: the preparation of carboxylic acid compound II. 17.26 g (100 mmol) of 3-hydroxy-4-chlorobenzoic acid, namely Dissolve in 300mL of dichloromethane, cool to 0°C, add 54.97g (200mmol) tert-butyldiphenylchlorosilane and 13.62g (200mmol) imidazole, stir magnetically, and react at room temperature for 20h. Add 100mL saturated ammonium chloride solution after the monitoring reaction finishes, separate liquids and get the organic phase, this organic phase and the aqueous phase are extracted with 300mL ethyl acetate, and the organic phase obtained by liquid separation is combined, and the solvent is removed by distillation under reduced pressure with a rotary evaporator. Cross column purification product, obtain 38.63g (94mmol) carboxylic acid compound II, namely .

[0034] The second step: the...

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Abstract

The invention provides a synthetic method of 1,2-dioxetane compound. The synthetic method includes the steps: A) preparation of a carboxylic compound II; B) preparation of an ester compound III; C) preparation of an enol methyl ether compound IV; D) preparation of a phenol compound V; E) preparation of a phosphate ester compound; and F) preparation of a target compound VII. The synthetic method of 1,2-dioxetane compound is short in synthesis route, few in step, mild in reaction condition, simple and convenient to operate and high in yield, and the synthesized 1,2-dioxetane compound is high in purity and fine in luminescent performance and can be used as substrate in chemiluminescence reaction to be applied to the technical field of chemiluminescence immunoassay.

Description

Technical field [0001] The present invention involves a synthesis method of a chemical luminous agent, especially the synthesis method of a 1,2-eoxidic alkane compound. Background technique [0002] The 1,2-dicotylexic compounds are a class of chemical light-emitting reactions in the field of chemical light-emitting immune analysis technology.1,2-CSPD, CDP, CDP-Star, BZPD, and its luminous liquid in CSPD, CDP, CDP-Star, BZPD, and Lumigen in 1,2-epoxyticotylene compounds.Applications.1,2-AMPPD in the borerhole compounds in the binocular ring is a key chemical luminous substrate used on the fully automated chemical light emitting immune analysis instrument. It can send a high-strength light signal. It is currently widely used as chemical light-emitting immune analysis.It has the highest detection sensitivity, stable detection results, and good repetitiveness. It has been promoted in medicine, but due to its high price, it limits its large -scale development and use.The main reason ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/655C09K11/07
Inventor 任琪谈宇清
Owner 广东派特埃尔生物科技有限公司
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