Synthetic method of 1,2-dioxetane compound

A technology for the synthesis of dioxetane and its synthesis method, which is applied in the field of synthesis of chemiluminescent agents, can solve problems such as difficulty in large-scale production, long synthesis route, complicated operation, etc., and achieve fewer steps, short synthesis route and high purity Effect

Active Publication Date: 2013-01-16
广东派特埃尔生物科技有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[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

Examples

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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 invention relates to a synthesis method of a chemiluminescent agent, in particular to a synthesis method of a 1,2-dioxetane compound. Background technique [0002] 1,2-dioxetane compounds are well-known in the field of chemiluminescent immunoassay techniques as substrates for chemiluminescent reactions. Most of CSPD, CDP, CDP-Star, BZPD and their luminescent liquids in 1,2-dioxetane compounds are patented products of foreign companies such as Tropix and Lumigen, which are expensive, which greatly limits the domestic use of this technology Applications. AMPPD in 1,2-dioxetane compound is the key chemiluminescent substrate used in automatic chemiluminescent immunoassay instruments, which can emit high-intensity light signals, and has been widely used in chemiluminescent immunoassays. It has the highest detection sensitivity, stable detection results, and good repeatability. It has been widely used in medicine, but its large-scale development and us...

Claims

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Application Information

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Patent Type & Authority Applications(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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