Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for efficiently synthesizing 1,6-diene-3-ketone derivatives

A technology of ketone derivatives and dienes, applied in the field of efficient synthesis of 1,6-dien-3-one derivatives, can solve the difficulties of 1,6-dien-3-one derivatives, harsh reaction conditions, pollution Environmental and other issues, to achieve the effect of novel structure, mild reaction conditions, and simple operation

Pending Publication Date: 2021-01-22
XUZHOU UNIV OF TECH +1
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there have been many reports on the synthesis of 1,6-dien-3-one derivatives, but the existing synthesis methods have defects such as harsh reaction conditions, complicated operations, and environmental pollution. To obtain new 1,6-dien-3-one derivatives En-3-one derivatives are difficult

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 efficiently synthesizing 1,6-diene-3-ketone derivatives
  • Method for efficiently synthesizing 1,6-diene-3-ketone derivatives
  • Method for efficiently synthesizing 1,6-diene-3-ketone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: preparation compound 1a

[0026] Bis(triphenylphosphine)palladium dichloride (0.35g, 0.5mmol) and ketone iodide (0.19g, 1mmol) were added into a 500mL Shrek bottle, and the solvent triethylamine ( 200mL), iodobenzene (11.22g, 55mmol) and 4-pentynol (4.2g, 50mmol), react at room temperature for 12 hours. Extracted with ethyl acetate, dried over anhydrous magnesium sulfate, suction filtered, concentrated under reduced pressure in vacuo, the eluent was ethyl acetate:petroleum ether=1:3, separated by column chromatography to obtain 4-pentyn-1-ol (7.6g , 95%).

[0027] 4-Pentyn-1-ol (7.6g, 47.5mmol) was dissolved in dichloromethane (50mL) solvent, and Dess Martin (22.2g, 52.3mmol) oxidant solid particles were slowly added at 0°C, and the temperature was raised to room temperature to continue React for 2 hours. The solid was removed by suction filtration, the filtrate was quenched with saturated aqueous sodium bicarbonate, extracted with dichloromethane, drie...

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 discloses a method for efficiently synthesizing 1,6-diene-3-ketone derivatives, which comprises the following steps: in an organic solvent system, taking a compound represented by a formula 2 as a raw material, carrying out stirring reflux reaction at 75-85 DEG C, carrying out TLC tracking reaction until the reaction is complete, and carrying out after-treatment on the reaction solution to obtain a compound represented by a formula 1. According to the invention, a series of substrate allene-7-alkyne-4-ketone is designed and synthesized for the first time through cascade reaction,the substrate is a synthon with multiple reaction sites and high functional group activity, no catalyst or oxidant is needed, and the 1,6-diene-3-ketone derivatives can be smoothly synthesized only in a solvent; the reaction has the advantages of simple operation, low price, novel structure and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for efficiently synthesizing 1,6-dien-3-one derivatives. Background technique [0002] 1,6-dien-3-one is an important organic synthesis intermediate. Due to the particularity of the product skeleton, it not only shows rich pharmacological activities in medicine, but also the new material synthesized has outstanding performance and can replace A variety of imported materials, such as photosensitive materials, charge transport materials, semiconductor bonding. In addition, it has broad application prospects in microelectronics, organic light-emitting semiconductors, optical devices, and the like. [0003] At present, there have been many reports on the synthesis of 1,6-dien-3-one derivatives, but the existing synthesis methods have defects such as harsh reaction conditions, complicated operations, and environmental pollution. To obtain new 1,6-dien-3...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/67C07C45/67C07C49/753C07C67/333C07C69/76C07C49/697C07D333/22C07D213/50C07F7/08
CPCC07C45/67C07C67/333C07D333/22C07D213/50C07F7/081C07F7/083C07C2602/06C07C49/67C07C49/753C07C69/76C07C49/697
Inventor 张天舒徐婷姜波
Owner XUZHOU UNIV OF TECH