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A kind of synthetic method of asymmetric conjugated diyne

A synthesis method and asymmetric technology are applied in the field of synthesis of asymmetric conjugated diacetylenes, which can solve the problems of unsuitability for industrial production, low reaction yield, high reaction cost and the like, and achieve the advantages of being beneficial to industrial production, mild reaction conditions, Good catalytic effect

Active Publication Date: 2018-08-17
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] The experimental method has wide substrate adaptability, but uses a bimetallic catalyst
[0023] In summary, although there are many methods for synthesizing conjugated diynes in the prior art, some of these methods need to go through relatively complicated synthesis steps; some of the reactants used are unstable, and the operation has certain difficulties; , and the reaction yield is low; some organic phosphine drugs are easy to cause environmental pollution
More importantly, most of these reactions use palladium, nickel and other noble metals or bimetals as catalysts, which are expensive and non-recyclable, and are not suitable for industrial production.

Method used

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  • A kind of synthetic method of asymmetric conjugated diyne
  • A kind of synthetic method of asymmetric conjugated diyne
  • A kind of synthetic method of asymmetric conjugated diyne

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] A synthetic method of asymmetric conjugated diacetylene includes the following steps:

[0066] A. Weigh 0.05mmol of shuttle-shaped nano-copper oxide, 0.15mmol of o-phenanthroline, and 2mmol of sodium hydroxide into a clean and dry reaction tube. Place the reaction tube in an anhydrous and oxygen-free system, vacuum and pass Enter argon for three cycles, and then add 1mmol cis-1-(2-bromovinyl)-4-tert-butylbenzene, 1.2mmol 1-ethynyl-4-methoxybenzene and 3mL under the protection of argon. Diethylene glycol dimethyl ether, stirring and refluxing at 140°C for 20 hours;

[0067] B. After stopping the reaction, cool to room temperature, extract 3 times with petroleum ether, 10mL petroleum ether each time, and dry the obtained organic phase with anhydrous magnesium sulfate, and after concentration, use petroleum ether as a developing solvent to separate and purify by column chromatography to obtain white The solid is 1-tert-butyl-4-[4-(4-methoxyphenyl)butane-1,3-diynyl]benzene, the...

Embodiment 2

[0075] A synthetic method of asymmetric conjugated diacetylene includes the following steps:

[0076] A. Weigh 0.05mmol of sea cucumber-shaped nano-copper oxide, 0.15mmol of o-phenanthroline, and 2mmol of potassium hydroxide into a clean and dry reaction tube. Place the reaction tube in an anhydrous and oxygen-free system, vacuum and pass Circulate three times with argon gas, and then add 1mmol cis-1-(2-bromovinyl)-4-methylbenzene, 1.2mmol 1-ethynyl-4-fluorobenzene and 3mL N, under the protection of argon gas. N-dimethylformamide was stirred and refluxed at 140°C for 20 hours.

[0077] B. After stopping the reaction, cool to room temperature, extract 3 times with petroleum ether, 10 mL petroleum ether each time, and dry the obtained organic phase with anhydrous magnesium sulfate and concentrate. Separation and purification by column chromatography with petroleum ether as the developing solvent gave a white solid, namely 1-fluoro-4-[4-(4-methylphenyl)butane-1,3-diynyl]benzene, with...

Embodiment 3

[0085] A synthetic method of asymmetric conjugated diacetylene includes the following steps:

[0086] A. Weigh 0.1mmol flake nano-copper oxide, 0.3mmol o-phenanthroline, and 4mmol sodium hydroxide into a clean and dry reaction tube, place the reaction tube in an anhydrous and oxygen-free system, vacuum and pass Enter argon for three cycles, and then add 2mmol cis-1-(2-bromovinyl)benzene, 2.4mmol 1-ethynyl-4-fluorobenzene and 4mL diethylene glycol dimethyl ether under the protection of argon. , Stir and reflux for 20 hours at 140°C;

[0087] B. After stopping the reaction, cool to room temperature, extract 3 times with petroleum ether, 10 mL petroleum ether each time, and dry the obtained organic phase with anhydrous magnesium sulfate and concentrate. Separation and purification by column chromatography with petroleum ether as a developing solvent is a white solid, namely 1-[4-(4-fluorophenyl)butane-1,3-diynyl]benzene, the yield is 61%, and the melting point is 121- 123°C.

[0088]...

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Abstract

The invention provides a synthesis method of asymmetric conjugated diyne. The synthesis method comprises the following steps of A, mixing a catalyst with phenanthroline and a strong base, then adding cis-alkenyl bromide, terminal alkyne and a solvent in an argon atmosphere, and agitating, refluxing and making an obtained mixture react for 20h to 24h under a condition of 140 to 150 DEG C; B, extracting, drying and concentrating a product, and then separating and purifying the product through column chromatography, so that the asymmetric conjugated diyne is obtained. Compared with the prior art, the synthesis method provided by the invention is low in cost, easy in the obtaining of raw materials, relatively convenient to operate, high in efficiency, wide in serviceable range and suitable for the reaction of multiple substrates; further, the catalyst can be recycled.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing an asymmetric conjugated diyne. Background technique [0002] Conjugated diacetylenes are important raw materials and intermediates in the field of organic synthesis, and can be used as starting materials for the synthesis of macrocyclic annunes, conjugated alkyne oligomers, etc. At the same time, it is the skeleton structure of a variety of natural products and biologically active compounds. Some compounds containing 1,3-diyne structure have been confirmed to have high anti-tumor, antibacterial, anti-inflammatory and anti-HIV activities. For example: 19-(2-furyl)-5,7-nonadecanadiynoic acid, a traditional Chinese medicine component isolated from Artemisia serrata. [0003] [0004] The methods for synthesizing asymmetric conjugated diynes reported in the literature mainly include the following: [0005] (1) In 2000, E. Negishi's research g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/30C07C43/215C07C43/225C07C17/269C07C25/24C07B37/00
CPCY02P20/584
Inventor 张武武超婷李倩李佳徐洋洋
Owner ANHUI NORMAL UNIV