Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Preparation method of 1, 2-dioxetane derivative

A technology for dioxetane and derivatives is applied in the field of preparation of 1,2-dioxetane derivatives, which can solve the problems of being unsuitable for industrial production, difficult for industrial application, unfavorable for industrial production, and the like, and achieves a high yield High, convenient for industrial production, production safety effect

Active Publication Date: 2015-11-25
SUZHOU YACOO SCI CO LTD
View PDF9 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chinese patent CN103772433A and CN200510021054 adopt 2-adamantanone and substituent-protected dimethyl / ethyl carbomethoxybenzyl methyl ether as raw material to obtain intermediate through Wittig reaction. This route also requires 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 reagents 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 1, 2-dioxetane derivative
  • Preparation method of 1, 2-dioxetane derivative
  • Preparation method of 1, 2-dioxetane derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 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 is dissolved in 1000mL of methyl tert-butyl ether to obtain a solution of the compound shown in formula II with a molar volume concentration of 0.5mol / L; then at a temperature of -40°C, add 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 the first sodium hydroxide solution was added, and the reaction was carried out for 2 hours. The molar ratio of the first sodium hydroxide to the compound shown in formula II was 1:1; then hydrochloric acid w...

Embodiment 2

[0031]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

[0033] 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 the...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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 number: 122341-56-4, common name 3-(2-spiroadamantane)-4-methoxy-4-(3-phosphoryloxy)-phenyl-1,2-dioxo Cyclohexane disodium salt (molecular formula is shown in formula I), is the latest ultrasensitive alkaline phosphatase substrate in the field of biochemistry, and has a wide range of applications in biological detection technology. [0003] [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), the key intermediate is prepared by McMurry reaction through 2-adamantanone and 3-hydroxybenzoic acid formic acid, the route is short, ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products