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Compound containing alkynyl, preparation method and application

A technology for compounds and carboxylate compounds, applied in the field of preparation of alkynyl esters of unsaturated carboxylic acids, can solve the problems of low activity of functional groups, increased separation and purification steps, low reaction conversion rate, etc.

Active Publication Date: 2017-04-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems of the indirect method are: (1) due to the low activity of the functional groups on the macromolecular chain, the reaction conversion rate is usually relatively low, which leads to a limited number of alkynyl groups introduced on the macromolecular chain; (2) the above-mentioned reaction usually Requires solvents, adding separation and purification steps, which in turn increases cost
Current research focuses on alkynolates, but few alkynyl esters are available

Method used

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  • Compound containing alkynyl, preparation method and application
  • Compound containing alkynyl, preparation method and application
  • Compound containing alkynyl, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0101] Preparation of 1-ethynyl-(3-methyl)-cyclopentanol:

[0102] Add 130 grams of potassium tert-butoxide and 100 ml of cyclohexane into a 300 ml round bottom bottle at room temperature, pass through acetylene gas, add 100 grams of 3-methylcyclopentanone dropwise, stir and react at 15°C for 2 hours, add 20 ml of water, After stirring for 10 minutes, transfer to a 500ml separatory funnel, separate the water phase, then wash three times with distilled water, dry the organic phase with anhydrous sodium sulfate, and remove the solvent under reduced pressure. The yield is 92%.

preparation example 2

[0104] 3-Methyl-1-yne-3-pentanol, 3-ethynyl-3-decanol, 2-(p-butoxyphenyl)-3-yne-2-butanol, 2-phenyl-3 -Alkyne-2-butanol, 1-ethynyl-(4-methylthio)cyclohexanol, 2-(thiophene)-3-alkyne-2-butanol, 1-ethynylcyclohexanol, 1-ethynyl The preparation of base cyclopentanol:

[0105] Replace 3-methylcyclopentanone with the ketone corresponding to the prepared alcohol, and the molar ratio of the ketone to potassium tert-butoxide is 1:1.1; other conditions are the same as in Preparation Example 1.

Embodiment 1

[0107] Acrylic acid (3-methyl-1-yne-3-pentyl) ester (R in the structural formula 1 =-CH 3 , R 2 =-C 2 h 5 , R 3 = R 4 =H, acid chloride esterification) preparation process is as follows:

[0108] In a 500ml round bottom flask with magnetic stirring, add 35g (0.36mol) 3-methyl-1-yne-3-pentanol, 200ml dichloromethane and 34g (0.33mol) triethylamine, cool in an ice bath Add 26g (0.28mol) of acryloyl chloride dropwise, and react overnight at room temperature after the dropwise addition is completed for 2 to 3 hours. Suction filter the crude product, transfer the filtrate into a 1000ml separatory funnel, add 200ml of dichloromethane to dilute, and then use saturated Wash twice with sodium bicarbonate solution, then wash twice with deionized water, use a rotary evaporator to remove most of the solvent and distill under reduced pressure to obtain a colorless transparent liquid with a yield of 95%. Compound obtained in Example 1 1 H-NMR spectrum see figure 1 . The characteri...

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Abstract

The invention discloses a compound containing alkynyl, a preparation method and application. The compound containing alkynyl is unsaturated carboxylic ester with an acetylene tertiary carbon group, the size of a substituent group on tertiary carbon of the unsaturated carboxylic ester is appropriate, and therefore the alkynyl does not participate in or influence the free radical polymerization reaction of carbon-carbon unsaturated double bonds, and the alkynyl can be completely reserved on a polymer molecule chain. Due to the adoption of the unsaturated carboxylic ester, a polymer with the alkynyl contained in the molecule chain can be obtained through one step of polymerization reaction without conducting protection or deprotection on the alkynyl.

Description

technical field [0001] The invention relates to an alkynyl-containing compound, a preparation method and an application thereof, in particular to an alkynyl ester of an unsaturated carboxylic acid, a preparation method and an application thereof. Background technique [0002] "Click" chemistry is a rapid and highly selective synthesis method, which has been widely used in the fields of drug synthesis, fine macromolecular construction, polymer surface modification or functionalization, biomaterial preparation, nanomaterials and functional coatings. "Click" chemical reactions include copper(I)-catalyzed azide-alkyne cycloaddition reactions, free radical addition reactions of thioynes. Compared with the azide-alkyne cycloaddition reaction, the thioyne reaction is safer. In addition, the thioyne reaction does not use metal catalysts, so it is more environmentally friendly and has great application value. Polymers containing alkyne groups in the molecular chain can be modified ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/03C07C67/08C07C67/14C07C321/22C07C319/20C07D333/16C08F220/18C08F220/14C08F238/00
CPCC07C67/03C07C67/08C07C67/14C07C319/20C07D333/16C08F220/18C08F220/1804C07C69/54C07C321/22C08F220/14C08F238/00
Inventor 王跃川刘宇
Owner SICHUAN UNIV
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