A kind of preparation method of conjugated diene compound

A conjugated diene and compound technology, which is applied in the field of fine chemicals and related chemistry, can solve problems such as high reaction temperature, and achieve the effects of easy availability of raw materials, cheap raw materials and mild conditions

Active Publication Date: 2020-04-07
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method not only requires a higher reaction temperature, but also the reaction substrate often requires pre-functionalization [Lee, P.H., Seomoon D., Lee K.Org.Lett., 2005,7,343-345]

Method used

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  • A kind of preparation method of conjugated diene compound
  • A kind of preparation method of conjugated diene compound
  • A kind of preparation method of conjugated diene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of 2,3-diphenyl-1,3-dibutene

[0038] In a 25mL reactor, add p-toluenesulfonic acid (0.029g, 0.15mmol), pivalic acid (0.087g, 0.85mmol), zinc powder (0.033g, 0.5mmol), tetrakis(triphenylphosphine) palladium (0.023 g, 0.02mmol), nitrogen replacement 3 times, add anhydrous dichloromethane 3mL, add phenylacetylene (0.051g, 0.5mmol) under stirring, stir at 25°C for 24h. Column chromatography (silica gel, 200-300 mesh; developer, petroleum ether) obtained 0.038 g of 2,3-diphenyl-1,3-dibutene with a yield of 73%.

[0039] 2,3-Diphenyl-1,3-dibutene

[0040] colorless crystals; 1 H NMR (CDCl 3 ,400MHz)δ7.38-7.40(m,4H),7.19-7.27(m,6H),5.53(s,2H),5.30(s,2H); 13 C NMR (CDCl 3 ,100MHz)δ149.9,140.2,128.2,127.6,116.4ppm; MS(EI)m / z=207,206,191,178,128,115,91.

Embodiment 2

[0041] Example 2: Synthesis of 2,3-bis(4-methylphenyl)-1,3-dibutene

[0042] The operation was the same as in Example 1, and 0.049 g of 2,3-bis(4-methylphenyl)-1,3-dibutene was obtained by reacting 4-methylphenylacetylene, with a yield of 83%.

[0043] 2,3-bis(4-methylphenyl)-1,3-dibutene

[0044] white solid; 1 H NMR (CDCl 3 ,400MHz)δ7.28(d,J=8.0Hz,4H),7.05(d,J=8.0Hz,4H),5.50(s,2H),5.26(s,2H),2.28(s,6H); 13 C NMR (CDCl 3 ,100MHz)δ149.8,137.4,137.2,128.9,127.3,115.4,21.2ppm; MS(EI)m / z=235,234,219,204,128,115,91

Embodiment 3

[0045] Example 3: Synthesis of 2,3-bis(4-methoxyphenyl)-1,3-dibutene

[0046] The operation was the same as in Example 1, and 0.060 g of 2,3-bis(4-methoxyphenyl)-1,3-dibutene was obtained from the reaction of 4-methoxyphenylacetylene, with a yield of 90%.

[0047] 2,3-bis(4-methoxyphenyl)-1,3-dibutene

[0048] white solid; 1 H NMR (CDCl 3 ,400MHz)δ7.31(d,J=8.0Hz,4H),6.78(d,J=8.0Hz,4H),5.47(s,2H),5.23(s,2H),3.74(s,6H); 13 C NMR (CDCl 3 ,100MHz)δ159.1,149.4,132.7,128.5,114.3,113.6,55.2ppm; MS(EI)m / z=267,266,251,235,121

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Abstract

The invention belongs to the field of fine chemicals and related chemical technologies, and provides a preparation method of butadiene derivatives. Using phenylacetylene and its derivatives as raw materials, under the action of metal catalysts and additives, react in anhydrous organic solvents to convert them into 2,3-disubstituted-1,3-butadiene compounds. The invention has the beneficial effects of simple and convenient operation, mild conditions, environmental friendliness, the possibility of realizing industrialization, and obtaining butadiene compounds with a relatively high yield; the butadiene compounds synthesized by the method can be further functionalized Various compounds are obtained, which are then applied to the development and research of natural products, functional materials and fine chemicals.

Description

technical field [0001] The invention belongs to the field of fine chemicals and related chemical technologies, and provides a preparation method of 1,3-butadiene derivatives. Background technique [0002] Conjugated diene derivatives are important components of many natural product molecules, and are also an important class of organic synthesis intermediates, widely used in Diels-Alder reactions, electrocyclization reactions, Ziegler-Natta polymerizations, etc. [MundalD.A. , Lutz K.E., Thomson R.J., Org. Lett., 2009, 11, 465-468]. Therefore, it is of great significance and application value to develop efficient and highly selective synthetic methods of conjugated dienes, especially 1,3-butadiene derivatives. At present, the methods for synthesizing 1,3-butadiene derivatives mainly include: Wittig reaction, transition metal-catalyzed cross-coupling reaction of alkenyl halides, and Pd-catalyzed oxidative coupling reaction of N-toluenesulfonyl hydrazone, etc. [0003] The Wit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C2/38C07C15/50C07C41/30C07C43/215C07C17/269C07C25/24C07C45/69C07C49/796C07D333/04
CPCC07C2/38C07C17/269C07C41/30C07C45/69C07C2523/44C07C2523/06C07C15/50C07C43/215C07C25/24C07C49/796C07C2/406C07C11/12C07C2527/185C07C2531/22C07C2531/24C07C2531/28
Inventor 包明郭宏宇张胜
Owner DALIAN UNIV OF TECH
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