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

Method for preparing (E)-1, 3-diphenyl-4-nitro-1-butene

A technology of diphenylpropylene and diphenyl, which is applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as long reaction time and high reaction temperature, and achieve the effects of simple operation, high yield and easy availability of raw materials

Active Publication Date: 2019-05-24
ZHEJIANG UNIV OF TECH
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two methods all have disadvantages such as the need to use transition metal palladium catalysts, functionalized substrates, higher reaction temperatures, and longer reaction times.
In addition, method 1 also requires the use of excess nitromethane, which can easily produce explosive substances under alkaline conditions

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
  • Method for preparing (E)-1, 3-diphenyl-4-nitro-1-butene
  • Method for preparing (E)-1, 3-diphenyl-4-nitro-1-butene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] At room temperature, dissolve 0.1943g (1.0mmol) (E)-1,3-diphenylpropene in 3mL 1,2-dichloroethane, add 0.1362g (0.6mmol) DDQ, stir for 10 minutes, add 0.05806g (0.5mmol) (E)-1-dimethylamino-2-nitroethylene was reacted for 2 hours, and then 0.1ml of 1mol / L hydrochloric acid aqueous solution was added to the reaction liquid, and the reaction was continued for 0.5 hours. After the reaction is over, add 30 g of 200-300 mesh silica gel to the reaction solution, remove the solvent under reduced pressure, and pass through the column. The developer used is petroleum ether: ethyl acetate = 30:1, and the colorless oily (E)-1,3 -Diphenyl-4-nitro-1-butene, yield 78%.

Embodiment 2

[0021] At room temperature, dissolve 0.1943g (1.0mmol) (E)-1,3-diphenylpropene in 3mL 1,2-dichloroethane, add 0.1362g (0.6mmol) DDQ, stir for 10 minutes, add 0.05806g (0.5mmol) (E)-1-dimethylamino-2-nitroethylene was reacted for 2 hours, and then 0.1ml of 1mol / L formic acid aqueous solution was added to the reaction liquid, and the reaction was continued for 0.5 hours. After the reaction was completed, 30 g of 200-300 mesh silica gel was added to the reaction solution, the solvent was removed under reduced pressure, and the solvent was passed through the column. The developer used was petroleum ether: ethyl acetate = 30:1, and the colorless oily (E)-1 was obtained by separation. 3-Diphenyl-4-nitro-1-butene, yield 75%.

Embodiment 3

[0023] At room temperature, dissolve 0.1943g (1.0mmol) (E)-1,3-diphenylpropene in 2mL 1,2-dichloroethane, add 0.1362g (0.6mmol) DDQ, stir for 10 minutes, add 0.05806g (0.5mmol) (E)-1-dimethylamino-2-nitroethylene was reacted for 2 hours, and then 0.1ml of 1mol / L acetic acid aqueous solution was added to the reaction liquid, and the reaction was continued for 0.5 hours. After the reaction was completed, 30 g of 200-300 mesh silica gel was added to the reaction liquid, the solvent was removed under reduced pressure, and the solvent was passed through the column. The developer used was petroleum ether: ethyl acetate = 30:1, and (E)-1 was separated as a colorless oil. 3-Diphenyl-4-nitro-1-butene, yield 73%.

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

A method for preparing (E)-1, 3-diphenyl-4-nitro-1-butene comprises the following steps: using (E)-1-dimethylamino-2-nitroethylene (I), (E)-1, 3-diphenyl propylene (II) as raw materials, using 1, 2-dichloroethane as a solvent, reacting at room temperature to be complete under the combined action of DDQ and an acidic catalyst, and then carrying out post-treatment on the reaction solution to obtaina target product (III); the method has the advantages of high yield, simple and safe operation, easily obtained raw materials and the like.

Description

(1) Technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of (E)-1,3-diphenyl-4-nitro-1-butene. (2) Background technology [0002] (E)-1,3-diphenyl-4-nitro-1-butene is an important intermediate in organic synthesis. Due to the strong electron-withdrawing effect of the nitro group, the compound can effectively construct carbon-carbon bonds, and the nitro group can also be converted into functional groups such as amino, carboxyl, and oxime. At present, there are mainly two methods for the synthesis reaction of (E)-1,3-diphenyl-4-nitro-1-butene: the first method is palladium-catalyzed coupling reaction of allyl acetate and nitromethane (J.Org.Chem.2006,71,8644-8646); Method two is that palladium catalyzes allylamine and ethyl nitroacetate to carry out coupling reaction, then carries out hydrolysis decarbonylation under the effect of alkali (Adv.Synth . Catal. 2016, 358, 1854-1858...

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): C07C201/12C07C205/04
Inventor 程冬萍邓志腾颜继忠
Owner ZHEJIANG UNIV OF TECH
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