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Synthesis method for asymmetric conjugate diyne compound

A synthesis method and compound technology, applied in the field of organic synthesis, can solve problems such as the lack of breakthrough in asymmetric conjugated diyne compounds, precious metals, and narrow application range of substrates.

Inactive Publication Date: 2015-10-28
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods still have the disadvantages of using excessive reaction substrates, precious metals, using toxic organic solvents and strong oxidants, and narrow scope of substrate application.
Furthermore, although copper-catalyzed Glaser coupling reactions have been discovered for nearly 150 years, they are only applicable to homomolecular coupling reactions
Its application in the synthesis of asymmetric conjugated diynes has not yet made a breakthrough

Method used

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  • Synthesis method for asymmetric conjugate diyne compound
  • Synthesis method for asymmetric conjugate diyne compound

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0024] Synthesis of 2-methyl-6-phenylhexa-3,5-diyn-2-ol

[0025] A mixed solvent consisting of 0.01mmol copper powder, 0.04mmol TMEDA, 0.2mmol 3-methylbutynol-3, 0.28mmol phenylacetylene, 0.4mL chloroform and 1,4-dioxane was added to the reactor (volume ratio is [3:1]). Heat to 50°C, continue to stir for 12 hours, stop the reaction, cool to room temperature, add saturated ammonium chloride solution to wash, extract with dichloromethane, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product. rate of 81%. 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.48-7.46(m,2H),7.35-7.30(m,3H),2.45(s,1H),1.58(s,6H).

Synthetic example 2

[0027] Synthesis of 2-methyl-6-(naphthalene-1-yl)hexa-3,5-diyn-2-ol

[0028] A mixed solvent composed of 0.02mmol copper powder, 0.04mmol TMEDA, 0.2mmol 3-methylbutynol-3, 0.28mmol 1-acetylene naphthalene, 0.4mL chloroform and 1,4-dioxane was added to the reactor ( The volume ratio is [3:1]). Heat to 50°C, continue to stir for 12 hours, stop the reaction, cool to room temperature, add saturated ammonium chloride solution to wash, extract with dichloromethane, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product. rate of 72%. 1 H NMR (400MHz, CDCl 3 ,TMS): δ8.32(d,J=8.3Hz,1H),7.85(d,J=8.2Hz,2H),7.74(dd,J=7.2,0.7Hz,1H),7.60-7.50(m, 2H),7.43-7.39(m,1H),2.23(s,1H),1.63(s,6H).

Synthetic example 3

[0030] Synthesis of 2-methyl-6-(p-tolyl)hexa-3,5-diyn-2-ol

[0031]Add 0.01mmol copper powder, 0.02mmol TMEDA, 0.2mmol 3-methylbutynol-3, 0.28mmol 4-ethynyltoluene, 0.4mL chloroform and 1,4-dioxane to the reactor (The volume ratio is [3:1]). Heat to 50°C, continue to stir for 12 hours, stop the reaction, cool to room temperature, add saturated ammonium chloride solution to wash, extract with dichloromethane, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product. rate of 72%. 1 H NMR (400MHz, CDCl 3 ,TMS): δ7.38(d,J=8.1Hz,2H),7.12(d,J=8.1Hz,2H),2.34(s,3H),2.28(s,1H),1.57(s,6H) .

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Abstract

The invention provides a synthesis method for asymmetric conjugate diyne compound. According to the synthesis method, two kinds of different terminal alkynes are used as raw material, copper is used as catalyst, and the asymmetric conjugate diyne compound is synthesized; the copper which is cheap and easy to get is used as the catalyst, reaction is conducted in the air, precious metal and additive are not needed, prefunctionalization on the alkynes is not needed, special reaction conditions such as microwave radiation are not needed, and the production cost is lowered; the reaction condition is mild, the operation is simple, the applicability of substrate is wide, both the selectivity and productivity of product are high, and good industrial application prospect is achieved.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing an asymmetric conjugated diyne compound. 【Background technique】 [0002] Asymmetric 1,3-conjugated diynes have rigid structural units and unique electronic properties. This type of compound structure is commonly found in natural products and antibacterial drugs. At the same time, it is also an important functional group in the synthesis of functional molecular materials. In addition, alkyne Coupling reactions have also been widely used in many synthetic chemistry fields, such as: synthesis of various types of alkynes, construction of macrocyclic alkynes, natural product synthesis and supramolecular applications, etc. Therefore, the synthesis method of asymmetric conjugated diynes is particularly important, and it is one of the difficulties in the research of organic synthesis and medicinal chemistry, and the exploration of the synthesis routes of such ...

Claims

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Application Information

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IPC IPC(8): C07B37/04C07C33/30C07C33/28C07C33/48C07C29/32C07C215/68C07C213/08C07D333/16C07C69/76C07C67/293C07F7/08C07C13/19C07C2/38C07C255/50C07C253/30C07C43/215C07C43/23C07C41/30C07C217/80C07C211/44C07C209/68
Inventor 周永波苏乐斌董建玉孙梦丽刘龙李中文尹双凤韩立彪
Owner HUNAN UNIV
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