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Synthesis method of 1,3-butadiyne compound

A synthesis method and compound technology, which is applied in the field of synthesis of 1,3-butadiyne compounds, can solve problems such as difficult recycling and complex oxidants, and achieve the effects of high overall yield, simple reaction route, and few side reactions

Inactive Publication Date: 2015-11-25
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The main defect that above method exists is: used expensive heavy metal and its compound, as nickel, cobalt etc.; Metal catalyst is easily soluble in organic solvent and is difficult to recycle; regular solvents, etc.

Method used

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  • Synthesis method of 1,3-butadiyne compound
  • Synthesis method of 1,3-butadiyne compound
  • Synthesis method of 1,3-butadiyne compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Take 0.0144g (0.10mmol) cuprous oxide (0.10mmol) of the catalytic system, 0.01803g (0.10mmol) of pullulan and 0.1020g (1mmol) of phenylacetylene, add 2mL dimethyl sulfoxide, stir and react at 90°C, and monitor the reaction process by TLC , After 2 hours, TLC monitors the disappearance of the raw material point, stops the reaction, filters, extracts the filtrate 3 times with deionized water, and concentrates by vacuum distillation to obtain the crude product, which is separated by column chromatography to obtain 1,4-diphenyl-1,3-butanedi Alkyne 0.0931g, yield 95%. Its NMR data are: 1 HNMR (400MHz, CDCl 3 ): δ =7.56(dd, J =9.5Hz, J =1.8Hz,4H),7.42-7.35(m,6H)ppm. 13 CNMR (100MHz, CDCl 3 ): δ =132.5, 129.3, 128.5, 121.8, 81.6, 73.9ppm.

Embodiment 2

[0025] Take the catalytic system cuprous oxide 0.0144g (0.10mmol), pullulan 0.01803g (0.10mmol) and p-ethylphenylacetylene 0.1311g (1mmol), add 2mL dimethyl sulfoxide, stir the reaction at 80°C, TLC Monitor the reaction process, after 2 hours, TLC monitors the disappearance of the raw material point, stop the reaction, filter, extract the filtrate 3 times with deionized water, and concentrate under reduced pressure to obtain the crude product, which is separated by column chromatography to obtain 1,4-di-p-ethylphenyl- 0.1207g of 1,3-butadiyne, yield 93%. Its NMR data are: 1 HNMR (400MHz, CDCl 3 ): δ =7.47(d, J =8.0Hz,4H),7.19(d, J =8.0Hz,4H),2.68(q, J =8.0Hz,4H),1.26(t, J =8.0Hz,6H)ppm. 13 CNMR (100MHz, CDCl 3 ): δ =145.8, 132.5, 128.1, 119.0, 81.6, 73.5, 29.0, 15.3ppm.

Embodiment 3

[0027] Take the catalytic system cuprous oxide 0.0144g (0.10mmol), pullulan 0.01803g (0.10mmol) and phenoxypropyne 0.1327g (1mmol), add 2mL dimethyl sulfoxide, stir the reaction at 90 ° C, TLC monitoring During the reaction, after 2.5 hours, TLC monitored the disappearance of the raw material point, stopped the reaction, filtered, extracted the filtrate 3 times with deionized water, concentrated under reduced pressure to obtain a crude product, and separated by column chromatography to obtain 1,6-diphenoxy-2, 0.1064g of 4-hexadiyne, yield 89%. Its NMR data are: 1 HNMR (400MHz, CDCl 3 ): δ =7.33(t, J =8.0Hz,4H),7.03(t, J =8.0Hz,2H),6.97(d, J =8.0Hz,4H),4.77(s,4H)ppm. 13 CNMR (100MHz, CDCl 3 ): δ =157.4, 129.6, 121.8, 114.9, 74.7, 71.0, 56.2ppm.

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Abstract

The invention discloses a synthesis method of a 1,3-butadiyne compound and belongs to the technical field of oxidative coupling reaction of an end group alkyne compound. The synthesis method disclosed by the invention is characterized by comprising the steps: sequentially adding a raw material end group alkyne compound, a catalytic system cuprous oxide and pullulan and a solvent dimethyl sulfoxide into a reaction container in sequence, heating to 80-110 DEG C, stirring till full reaction by monitoring of a TLC, filtering a reaction liquid, filtering residue, cleaning with ethyl acetate to obtain the catalytic system cuprous oxide and pullulan which can be repeatedly circularly used, extracting filtrate with deionized water, after drying with anhydrous sodium sulfate, distilling under reduced pressure and concentrating to obtain a crude product, and purifying the crude product through column chromatography on silica gel to obtain the 1,3-butadiyne compound. The catalytic system is low in price and easy to obtain, a reaction route is simple, side reactions are less, a substrate is wide in applicable range, the total yield is high, and the catalytic system is easy to separate and can be regenerated and recycled for use.

Description

technical field [0001] The invention belongs to the technical field of oxidative coupling reaction of terminal alkyne compounds, and in particular relates to a synthesis method of 1,3-butadiyne compounds. Background technique [0002] 1,3-Butadiyne is a kind of important functional group, which is a conjugated diyne formed from terminal alkynes. This kind of reaction is a powerful method to build carbon-carbon bonds. The conjugated structure constructed by this kind of reaction is a special kind of carbon-carbon bond and an important functional group. It has great application potential in sensors and fine organic synthesis, and its product conjugated diyne can play a considerable role as a scaffold molecule in many reactions. In the past 100 years, many catalytic systems have been found for this reaction, mainly including palladium, nickel, copper and gold. [0003] Beifuss et al. used CuCl as a catalyst, air as an oxidant, DBU as a base, and TMEDA as a ligand to complete ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/50C07C2/84C07C41/30C07C43/215C07C43/205C07C17/269C07C25/24
Inventor 姜玉钦郭妞李兴丰李星何兴董文佩徐桂清李伟
Owner HENAN NORMAL UNIV
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