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Preparation method of conjugated diene compound

A technology of conjugated dienes and compounds, which is applied in fine chemicals and related chemical fields, can solve problems such as high reaction temperature, and achieve the effect of easy-to-obtain, cheap raw materials and environmental friendliness

Active Publication Date: 2018-01-09
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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  • Preparation method of conjugated diene compound
  • Preparation method of conjugated diene compound
  • 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 relevant chemical technologies and provides a preparation method of a butadiene derivative. The preparation method comprises the following steps of by taking phenylacetylene and a derivative thereof as raw materials, under the actions of a metal catalyst and an additive, performing reaction in an anhydrous organic solvent, and converting thephenylacetylene and the derivative thereof to a 2,3-di-substituted-1,3-butadiene compound. The preparation method has the beneficial effects of being simple and convenient to operate and mild in condition, being environmental friendly, having the possibility of realizing industrialization, and preparing the butadiene compound with a higher yield. The butadiene compound synthesized by utilizing the method can perform further functionalization to obtain various compounds, and then the compounds are applied to development and study of natural products, functional materials and the 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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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