A kind of preparation method of 1,2-dioxane derivatives

A technology of dioxetane and its derivatives, which is applied in the field of preparation of 1,2-dioxetane derivatives, can solve the problems of not being suitable for industrialized production, unfavorable for industrialized production, difficult for industrialized application, etc., and achieve high yield High, convenient for industrial production, and the effect of reducing production costs

Active Publication Date: 2018-07-31
SUZHOU YACOO SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chinese patents CN103772433A and CN200510021054 use 2-adamantanone and substituent-protected dimethyl / ethoxybenzyl phosphate as raw materials to obtain intermediates through the Wittig reaction. This route also requires a lower operating temperature (- 70 to -50 degrees), is also not conducive to industrial production
[0006] Chinese patent (CN103951704A) uses adamantane-2-aldehyde and 3-hydroxyl-protected phenyl Grignard reagent as raw materials to synthesize key intermediates. The synthetic route used is relatively long, and it is also not easy for industrial application.
U.S. Patents US4956477, US6417380 and US6124478, use cyano-substituted adamantane to prepare key intermediates through Grignard reaction, and use highly toxic cyanide in the process, making this process route also unsuitable for industrial production

Method used

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Examples

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Comparison scheme
Effect test

Embodiment 1

[0027] A method for preparing a 1,2-dioxetane derivative, the 1,2-dioxetane derivative is a compound shown in formula I, and the preparation method comprises the following steps: taking the compound shown in formula II 198g (0.5mol) of the compound was dissolved in 1000mL of methyl tert-butyl ether to obtain a solution of the compound represented by formula II with a molar volume concentration of 0.5mol / L; then at a temperature of -40°C, 0.5mol The mixture of sodium hydride and 0.5mol adamantanone was then warmed up to room temperature and reacted for 10 hours; adding hydrochloric acid to adjust the pH value to 7.1, separating the organic layer, and then removing methyl tert-butyl ether by rotary evaporation to obtain the reactant; The reactant was dissolved in methanol, then added the first sodium hydroxide solution, and reacted for 2 hours, and the molar ratio of the first sodium hydroxide to the compound shown in formula II was 1: 1; then adding hydrochloric acid to adjust t...

Embodiment 2

[0034] A method for preparing 1,2-dioxetane derivatives. The substances of formula I, formula II, formula III and formula IV in this example are all the same as those in Example 1. The 1,2-dioxetane The cyclohexane derivative is a compound shown in formula I, and its preparation method comprises the steps of: taking the compound shown in formula II and dissolving it in an organic solvent to obtain the compound shown in formula II with a molar volume concentration of 0.4mol / L Then at a temperature of -20°C, add the mixture of alkali metal salt and adamantanone, then warm up to room temperature, and react for 10 hours, the moles of the compound shown in the formula II, alkali metal salt, and adamantanone The ratio is 1:0.9:0.9; add hydrochloric acid to adjust the pH value to 6.8, separate the organic layer, and then remove the organic solvent by rotary evaporation to obtain the reactant; dissolve the reactant with methanol, then add the first sodium hydroxide solution, and react ...

Embodiment 3

[0036] A preparation method of 1,2-dioxetane derivatives, the 1,2-dioxetane derivatives are compounds shown in formula I, formula I, formula II, formula The substances of III and Formula IV are all the same as in Example 1, and their preparation method comprises the steps of: taking the compound shown in Formula II and dissolving it in an organic solvent to obtain the compound shown in Formula II with a molar volume concentration of 0.6mol / L solution; then at a temperature of 20°C, add a mixture of alkali metal salt and adamantanone, then warm up to room temperature, and react for 12 hours. The molar ratio of the compound, alkali metal salt, and adamantanone shown in the formula II 1: 1.1: 1.1; add hydrochloric acid to adjust the pH value to 7.5, separate the organic layer, and then remove the organic solvent by rotary evaporation to obtain the reactant; dissolve the reactant with methanol, then add the first sodium hydroxide solution, and react 2.5 hours, the molar ratio of t...

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Abstract

The invention relates to a preparation method of a 1, 2-dioxetane derivative. The 1, 2-dioxetane derivative is a compound shown in a formula I. The preparation method comprises the following steps of taking a compound shown in a formula II and adamantanone; performing Wittig reaction to synthesize a compound shown in a formula III; performing phosphorylation to obtain a compound shown in a formula IV; and performing oxidation reaction to obtain the 1, 2-dioxetane derivative. The preparation method of the 1, 2-dioxetane derivative has the advantages that safety is high; production cost is low; and industrial production of the 1, 2-dioxetane derivative is facilitated.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 1,2-dioxetane derivatives. Background technique [0002] AMPPD, CAS No.: 122341-56-4, common name 3-(2-spiroadamantane)-4-methoxy-4-(3-phosphoryloxy)-phenyl-1,2-diox Cyclohexane disodium salt (see formula I for molecular formula) is the latest ultrasensitive alkaline phosphatase substrate in the field of biochemistry and has been widely used in biological detection technology. [0003] (Ι) [0004] The existing synthesis of AMPPD is generally completed according to the following process scheme: substituted phenylmethoxymethyladamantane (intermediate) is obtained from commercial raw materials, and then AMPDD is prepared through phosphonylation and photooxidation. European Patent (Patent No. EP0518387), using 2-adamantanone and 3-hydroxybenzoic acid as raw materials to prepare key intermediates through McMurry reaction, the route is short, requiring a lo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/655
Inventor 曹丽辉袁永坤卞福江郭华邱金锐刘文
Owner SUZHOU YACOO SCI CO LTD
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