Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 1,4-disubstituted-1,3-butadiyne

A diacetylene and disubstituted technology, applied in the field of organic synthesis, to achieve the effects of high yield, low production cost and easy source

Inactive Publication Date: 2017-12-26
佛山煜新科技有限公司
View PDF5 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent CN105085157A and patent CN105016947A respectively report a method for catalytically synthesizing 1,3-butadiyne using cuprous oxide / pullulan, or copper carboxymethylcellulose (II), which does not use alkali, However, copper catalysts or additives prepared using specific methods are required

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 1,4-disubstituted-1,3-butadiyne
  • Preparation method of 1,4-disubstituted-1,3-butadiyne
  • Preparation method of 1,4-disubstituted-1,3-butadiyne

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0028] Example 1-10 Optimization of reaction conditions

[0029] Using phenylacetylene as the raw material for the reaction, the reaction was carried out under air conditions. The effects of different catalysts, solvents and other reaction conditions on the reaction effect were explored, and representative examples 1-10 were selected. The results are shown in Table 1:

[0030]

[0031] Table I:

[0032] Example

Catalyst (mol%)

Solvent

T ( o C)

Yield (%)

1

CuI(10 mol %)

DMSO

100

45

2

CuI(10 mol %)

DMF

100

37

3

CuI(10 mol %)

MeOH

100

12

4

CuI(10 mol %)

DCM

100

5

5

CuI(10 mol %)

Dioxane

100

93

6

CuI(10 mol %)

Dioxane

60

71

7

CuI(20 mol %)

Dioxane

100

95

8

CuCl(10 mol %)

Dioxane

100

63

9

CuBr(10 mol %)

Dioxane

100

72

10

CuOTf(10 mol %)

Dioxane

100

56

[0033] The basic reaction conditions are as follows: 0.4 mmol of phenylacetylene, 2 mL of solvent, and reaction time of 12 hours.

[0034] Taking Example 5 as an example, the specific operation is as follows: add 40.8 mg (0.4 mmol) ...

Embodiment 6

[0036] The difference between Example 6 and Example 5 lies in the reaction temperature. From Example 6, it can be seen that when the reaction temperature drops to 60°C, the target product 1,4-diphenyl-1,3-butadiyne is The yield dropped to 71% accordingly.

Embodiment 7

[0037] The difference between Example 7 and Example 5 lies in the amount of catalyst added. It can be seen from Example 7 that when the amount of catalyst added is 20 mol %, the target product 1,4-diphenyl-1,3- The yield of diacetylene is not significantly improved. From the perspective of production cost, the present invention selects 10 mol% of the catalyst as the optimal feeding amount.

[0038] Examples 8-10 further screened other monovalent copper catalysts, and the results showed that the catalytic effects of cuprous chloride, cuprous bromide and CuOTf on the reaction were not as good as cuprous iodide.

[0039] Taking the reaction conditions of Example 5 as the optimal conditions, the substrate expansion reaction was carried out, and a series of 1,4-disubstituted-1,3-butadiyne compounds were obtained.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 1,4-disubstituted-1,3-butadiyne. The preparation method comprises the following steps: adding a substituted acetylene compound as shown in Formula I, cuprous iodide and a solvent 1,4-dioxane into a dried reactor, and performing a reaction with stirring in air at a certain temperature; and after the reaction is completed, filtering the reaction solution through a silica gel-containing glass dropper, performing rinsing with ethyl acetate, performing centrifugal drying on the filtrate, and performing separation through column chromatography to obtain the 1,4-disubstituted-1,3-butadiyne compound as shown in Formula II, wherein the reaction formula is shown in the specification.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a preparation method of 1,4-disubstituted-1,3-butadiyne. Background technique [0002] 1,4-Disubstituted-1,3-butadiyne compounds contain two special conjugated carbon-carbon triple bonds, which have been widely used in conjugated polymer light-emitting materials. At the same time, the structure It plays an important role in the synthesis of natural products, the preparation of electron transport materials, the synthesis of dye compounds and the synthesis of biologically active molecules. Therefore, the synthesis of 1,4-disubstituted-1,3-butadiyne compounds has become a research hotspot in the fields of organic synthesis, catalytic chemistry and materials chemistry. [0003] In 1869, Glaser used cuprous chloride in a solution of ammonia and ethanol to promote self-coupling reaction of phenylacetylene to produce 1,4-diphenyl-1,3-butadiyne. This is organic synthesis. The class...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C2/76C07C15/54C07C45/72C07C47/548C07C41/30C07C43/215C07D333/08C07C17/269C07C25/24
CPCC07C2/76C07C17/269C07C41/30C07C45/72C07D333/08C07C15/54C07C47/548C07C43/215C07C25/24
Inventor 武晓云
Owner 佛山煜新科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com