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

Phloroglucinol acetyl derivative and its synthesis method and uses

An acylation and reaction technology, applied in the field of phloroglucinol acetyl derivatives and synthesis thereof, can solve problems such as no reports on biological activity testing

Inactive Publication Date: 2006-02-08
BIOLOGY INST OF SHANDONG ACAD OF SCI
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no report on the synthesis method and biological activity test of the product modified by diacetylphloroglucinol in the relevant literature

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
  • Phloroglucinol acetyl derivative and its synthesis method and uses
  • Phloroglucinol acetyl derivative and its synthesis method and uses
  • Phloroglucinol acetyl derivative and its synthesis method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 2-Acetyl-4-propionylphloroglucinol, the molecular formula is:

[0018]

[0019] Synthesis of 2-acetyl-4-propionylphloroglucinol:

[0020] In a 250ml three-neck flask equipped with a stirring device and a reflux condenser, add 10g (0.060mol) 2-acetylphloroglucinol, and slowly add 9.2ml (0.071mol, 9.30g) propionic anhydride dropwise under nitrogen protection, Add 22.6ml (25.5g) of boron trifluoride-diethyl ether solution dropwise under stirring condition, including 0.18mol of boron trifluoride. . After the reaction is over, add 100ml of distilled water, stir for 5-10min, separate the reaction solution, extract the water layer with 50ml of ethyl acetate, combine the ester layer with the reaction solution, distill off the solvent under reduced pressure, and recrystallize the obtained solid with 60% ethanol / water The crude product was obtained, and the yield of the crude product was 78.9%. Using a developer of 3:1 n-hexane / ethyl acetate solution, the above crude produc...

Embodiment 2

[0023] 2-Acetyl-4-butyrylphloroglucinol, the molecular formula is:

[0024]

[0025] Synthesis of 2-acetyl-4-butyrylphloroglucinol:

[0026] In a 250ml three-necked flask equipped with a stirring device and a reflux condenser, add 5g (0.03mol) of 2-acetylphloroglucinol, and place the three-necked flask in an ice-salt bath so that the reaction temperature is not higher than 5°C, slowly Add 5.8ml (0.036mol, 5.65g) of butyric anhydride, then add 13.1ml (14.79g) of boron trifluoride-ether solution, in which boron trifluoride is 0.104mol, after the dropwise addition, add 10ml of anhydrous ether to make the reaction The substance was completely dissolved, and the reaction temperature was kept at -2-2°C and stirred for 24 hours. After the reaction, add 15ml of distilled water, stir vigorously, then add 30ml of 1:1 methanol / water, carefully add 10gK 2 CO 3 , make the solution pH=7-8, then add 10ml of 1:1 methanol / water, stir at room temperature for 6h, add 10% hydrochloric acid ...

Embodiment 3

[0029] As described in Example 1, the difference is that 0.060 mol of 2-acetylphloroglucinol, 0.085 mol of propionic anhydride, and 0.24 mol of boron trifluoride (diethyl ether solution) were added. The crude product yield was 82.4%, and the crude product was separated to obtain a pure product yield of 68%.

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

Disclosed is phloroglucinol acetyl derivative and its synthesis method and uses, wherein the derivative has the general formula disclosed in the specification, wherein R1 is -CH2CH3 or -CH2CH2CH3. The compound is prepared through one step alkylation reaction at the presence of Friedel catalyst by using phloroglucinol or 2-acetyl phloroglucinol as raw material. The compound provided by the invention can be used for the prevention and treatment of plant diseases including cotton soreshin, Rhizoctonia cerealis, chloranemia, apple ring spot, grape botrytis bunch rot and blight, wilt, Leuconostoc, black rot, and drechslera teres (sacc.) shoemaker.

Description

(1) Technical field [0001] The invention relates to a phloroglucinol acetyl derivative and its synthesis method and application, belonging to the technical field of biological antibiotic phloroglucinol acetyl derivatives. (2) Background technology [0002] 2,4-Diacetylphloroglucinol is a polyketide antibiotic with broad-spectrum bactericidal effect produced by Pseudomonas fluorescens. It has strong killing activity against bacteria, fungi, viruses and worms, and is also effective against higher Plants have certain toxicity, see the patent "Pseudomonas fluorescens, bacterial agent for disease prevention and preservation of fruits and vegetables and its production process" announcement number 1403568; Bender et al., polyketide antibiotics produced by Pseudomonas fluorescens, Acta Phytopathology, Vol. 37, 175-196, 1999 (Bender, C.L, et.al.1999. Polyketide production by plant-associated Pseudomonas. Ann. Rev. Phytopathol. 37: 175-196); Wang Ye, Antibiotic Production 2, Isolatio...

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): C07C49/78A01N35/04
Inventor 高永超孔学杨合同王加宁陈贯虹聂玉敏
Owner BIOLOGY INST OF SHANDONG ACAD OF SCI
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