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Synthetic method of 1, 2-dioxetane compound

A technology of dioxetane and a synthesis method, applied in the field of chemiluminescence substrate synthesis, can solve problems such as difficulty in realizing large-scale production, difficulty in separation and purification, complicated process, etc., achieve easy process amplification and industrialization, and improve reaction Yield, effect of improving reaction conditions

Inactive Publication Date: 2013-05-01
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This preparation method is complex in process, and the preparation of intermediates requires multi-step reactions, separation and purification are relatively difficult, the yield is low, and it is difficult to realize 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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Effect test

Embodiment 1

[0027] Example 1: Preparation of [(3-hydroxyl-4-chlorophenyl)methoxymethylene]-5-chloroadamantane: TiCl 4 / Li catalyst system

[0028] At room temperature (25°C), add 40mL of ethyl acetate to a 100mL three-necked flask, blow in nitrogen, and add 4.4mL of anhydrous TiCl 4 (40mmol), stir, obtain pale yellow liquid, add 0.56g (80mmol) metallic lithium, put three-necked bottle in ultrasonic cleaner, make the liquid level in the reaction flask slightly lower than the liquid level of water in the cleaning tank. Turn on the ultrasonic cleaner, and conduct an ultrasonic reaction at 25KHz for 15 minutes to obtain a black-purple liquid. Take out the three-necked bottle from the ultrasonic cleaner, add 15ml of triethylamine, and slowly add 5-chloro-2-adamantanone (20mmol) and 4-chloro-3 -Methyl hydroxybenzoate (20mmol) mixed solution, continue to reflux for 1h after adding, cool to room temperature, extract the reaction mixture three times with saturated sodium bicarbonate solution, an...

Embodiment 2

[0030] Example 2: Preparation of [(3-hydroxyl-4-chlorophenyl)methoxymethylene]-5-chloroadamantane: TiCl 4 / Al catalyst system

[0031] At room temperature, add 40mL tetrahydrofuran to a 100mL three-necked flask, blow nitrogen into it, and add 4.4mL anhydrous TiCl 4 (40mmol), stir, obtain pale yellow liquid, add 2.16g (80mmol) Al powder, put three-neck bottle in the ultrasonic cleaner, make the liquid level in the reaction bottle slightly lower than the liquid level of the water in the cleaning tank. Turn on the ultrasonic cleaner and react at 25KHz for 15min to obtain a black-purple liquid. Take out the three-neck bottle from the ultrasonic cleaner, add 15ml of triethylamine, and slowly add 5-chloro-2-adamantanone (20mmol) and 4-chloro-3-hydroxyl dissolved in 20mL of tetrahydrofuran dropwise under reflux Methyl benzoate (30mmol), continued to reflux for 2h after the addition, cooled the reaction solution to room temperature, extracted three times with ethyl acetate, combined...

Embodiment 3

[0033] Example 3: Preparation of [(3-hydroxyl-4-chlorophenyl)methoxymethylene]-5-chloroadamantane: TiCl 4 / Mg catalytic system

[0034] At room temperature, add 40mL ethyl acetate to a 100mL three-necked flask, blow nitrogen, and add 4.4mL anhydrous TiCl 4 (40mmol), stir, obtain light yellow liquid, add 1.92g (80mmol) Mg powder, put three-necked bottle in the ultrasonic cleaner, make the liquid level in the reaction bottle slightly lower than the liquid level of the water in the cleaning tank. Turn on the ultrasonic cleaner and react at 40KHz for 15min to obtain a black-purple liquid. Take out the three-necked bottle from the ultrasonic cleaner, add 15ml of triethylamine, and slowly add 5-chloro-2-adamantanone (20mmol) and 4-chloro-3 -Methyl hydroxybenzoate (40mmol), continue to reflux for 2h after addition, after cooling the reaction mixture to room temperature, extract three times with saturated aqueous sodium bicarbonate solution, combine the organic layers and wash with ...

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Abstract

The invention discloses a synthetic method of a 1, 2-dioxetane compound. The method takes 5-chloro-2-adamantanone and 4-chloro-3-methyl hydroxybenzoate as the raw materials, and includes the steps of reacting to prepare substituted phenyl methoxymethene adamantine in an organic solvent under ultrasonic and the actions of a catalyst and triethylamine; and subjecting substituted phenyl methoxymethene adamantine to a photosensitized oxidation reaction to prepare the 1, 2-dioxetane compound. The new catalytic systems used in the method include general goods all in mass production, therefore the risk is low, and technical magnification and industrialization are easy to achieve; compared with the traditional organic synthesis method, the synthetic method adopts ultrasound irradiation, so that reaction conditions can be improved, the reaction temperature can be reduced, the reaction can be accelerated, and the reaction yield can be improved.

Description

(1) Technical field [0001] The invention relates to the synthesis of chemiluminescent substrates, in particular to a synthesis method of 1,2-dioxetane compounds. (2) Background technology [0002] Chemiluminescence analysis technology has the advantages of high sensitivity, wide detection range, good specificity, rapid determination, etc., and has been widely valued by the medical and biological circles. Chemiluminescence detection uses the light energy generated when a substance undergoes a chemical reaction, that is, the energy released when the excited state returns to the ground state. The luminous intensity, that is, the reaction sensitivity, depends on the quantum yield of the transition. However, the currently widely used chemiluminescent reagents in China mainly include luminol and trichlorophenyl oxalate. They generally have the defect of low quantum efficiency. The quantum efficiency of the former is only 1% to 2%, and the latter is the highest Only around 25%. A...

Claims

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Application Information

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IPC IPC(8): C07F9/655
Inventor 焦艳华何睿梁媛媛陈灿玉章鹏飞
Owner HANGZHOU NORMAL UNIVERSITY
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