Pyrazolone Compound Stability via Electron Withdrawing Groups

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Solution Overview

Problem

The pyrazolonated compounds obtained by modifying the formyl group of sugar using 3-methyl-1-phenyl-5-pyrazolone as a pyrazolone compound are found to be easily decomposed and have low stability.

Innovation Solution

Introducing an electron withdrawing group in specific positions of the pyrazolone compound leads to the formation of a pyrazolonated compound with high stability, achieved by modifying the formyl group using this modified pyrazolone compound.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If 3-methyl-1-phenyl-5-pyrazolone is used to modify the formyl group of sugar, then the pyrazolonated compound can be obtained, but the compound has low stability and is easily decomposed

Engineering Contradiction:
Improvestability of pyrazolonated compoundVSAvoidstructural integrity of pyrazolonated compound
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the pyrazolone compound through the introduction of electron-withdrawing groups at specific positions (R1 and R3). This structural parameter change enhances the stability of the pyrazolonated compound by altering the electronic distribution and reducing susceptibility to decomposition, directly resolving the stability issue while maintaining the pyrazolonation function.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If electron withdrawing group is introduced in specific positions of pyrazolone compound, then the stability of pyrazolonated compound is improved, but the complexity of pyrazolone compound structure increases

Engineering Contradiction:
Improvestability of pyrazolonated compoundVSAvoidstructural complexity of pyrazolone compound
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies local quality by introducing electron-withdrawing groups at specific localized positions (R1 and R3) of the pyrazolone ring rather than modifying the entire molecule. This targeted approach improves stability through localized electronic effects while minimizing overall structural complexity, as only specific positions are modified rather than the whole molecular framework.

Inventive Principle:
Principle #3Local quality

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The resulting pyrazolonated compounds exhibit high stability, resisting decomposition and maintaining their structural integrity over time.

Implementation Method 1

a pyrazolonated compound with high stability can be obtained by modify a formyl group using pyrazolone in which an electron withdrawing group is introduced in specific positions

Methodology Applied
Scientific EffectElectron withdrawing group effect:

Data Source

PatentEP4563572A1Pyrazolone compound and pyrazolone agent
Publication Date: 2025.06.04 NOGUCHI INST
  • EP4563572A1 patent drawingFigure 1~3
  • EP4563572A1 patent drawingFigure 4~5
  • EP4563572A1 patent drawing

AI summary

The object of present invention is to provide pyrazolonated compounds with high stability. The object can be solved by a pyrazolone compound represented by the following formula (1): wherein R1 is an electron withdrawing group selected from the group consisting of one or more selected from the group consisting of a halogen atom, a nitro group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a perfluoropolyether group having 2 to 10 carbon atoms, and the following formulas (2) to (7): R2 is a hydrocarbon group having 1 to 1000 carbon atoms, which may contain a heteroatom, and n is an integer of 0 to 2.