67687-94-9

Basic information

• Product Name: (4Z)-1,3-dimethyl-2,6-diphenylpiperidin-4-one oxime
• CAS NO: 67687-94-9
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.3908
• Mol File: 67687-94-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 441.3°C at 760 mmHg
• Flash Point: 220.7°C
• Density: 1.11g/cm³
• Vapor Pressure: 1.45E-08mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: (4Z)-1,3-dimethyl-2,6-diphenylpiperidin-4-one oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (4Z)-1,3-dimethyl-2,6-diphenylpiperidin-4-one oxime(67687-94-9)
• EPA Substance Registry System: (4Z)-1,3-dimethyl-2,6-diphenylpiperidin-4-one oxime(67687-94-9)

Safety Data

• Hazardous Substances Data: 67687-94-9(Hazardous Substances Data)

Usage

Description

(4Z)-1,3-dimethyl-2,6-diphenylpiperidin-4-one oxime, also known as DMPPDPO, is a chemical compound with the molecular formula C19H22N2O. It is a piperidinone derivative featuring a nitroxyl moiety, which contributes to its potential pharmaceutical applications. DMPPDPO possesses antioxidant, neuroprotective, and anti-inflammatory properties, making it a promising candidate for various medical uses.

Uses

Used in Pharmaceutical Applications:
DMPPDPO is used as a nitroxyl radical scavenger for its antioxidant properties, which can help protect cells from oxidative stress and damage. This application type is beneficial in the treatment of various conditions where oxidative stress plays a significant role.
Used in Anti-Inflammatory Applications:
As a potential anti-inflammatory agent, DMPPDPO is utilized to alleviate inflammation and reduce swelling. This application is particularly useful in the treatment of various inflammatory conditions, such as arthritis and other autoimmune diseases.
Used in Neuroprotection:
Due to its neuroprotective properties, DMPPDPO is investigated for its potential use in protecting neurons from damage and degeneration. This application type is crucial in the development of treatments for neurodegenerative diseases like Alzheimer's, Parkinson's, and multiple sclerosis.
Used in Organ Preservation:
DMPPDPO has been studied for its potential use in organ preservation, which could help improve the success rate of organ transplants and extend the viability of organs outside the body.
Used in Anticancer Applications:
Although further research is needed, DMPPDPO has been investigated for its potential as an anti-cancer agent. Its antioxidant and anti-inflammatory properties may contribute to its effectiveness in combating cancer cells and reducing tumor growth.

Upstream product

• 5554-58-5 1,3-dimethyl-2,6-diphenylpiperidin-4-one 
• 5554-57-4 2,6-diphenyl-3-methyl-4-piperidone 
• 100-52-7 benzaldehyde 
• 5554-58-5 cis-2,6-diphenyl-trans-3,N-dimethylpiperidin-4-one 

Downstream Products

• 74693-39-3 4α-amino-1,3-dimethyl-2,6-diphenylpiperidine 
• 74693-39-3 4β-amino-1,3-dimethyl-2,6-diphenylpiperidine 
• 113849-92-6 4,5,6,7-tetrahydro-5,7-dimethyl-4,6-diphenylpyrrolo<3,2-c>pyridine 
• 113849-88-0 5,7-dimethyl-1-vinyl-4,6-diphenylpyrrolo<3,2-c>piperidine 
• 113849-91-5 3aH-3a,5-dimethyl-4,6-diphenylpyrrolo<3,2-c>piperidine 
• 5554-58-5 1,3-dimethyl-2,6-diphenylpiperidin-4-one 

Relevant articles and documents

Synthesis, spectral and antimicrobial evaluation of some novel 1-methyl-3-alkyl-2,6-diphenylpiperidin-4-one oxime carbonates

Synthesis of some novel biologically active piperidin-4-one oxime carbonates from 1-methyl-3alkyl-2,6-diphenylpiperidin-4-one oximes and substituted chloroformates was carried out in the presence of potassium carbonate as base and tetrabutylammonium bromide (TBAB) as catalyst. The newly synthesized compounds were characterized by IR, 1H, 13C NMR and LC-mass spectra. Based on the 1H NMR analysis, all the compounds were found to adopt normal chair conformation with equatorial orientation of all the substituents. For all the synthesized compounds (5a-5l) antimicrobial activity has been tested against bacterial and fungal strains using Streptomycin and Amphotericin B as standards.

Synthesis, stereochemistry, and?antimicrobial evaluation of?substituted piperidin-4-one?oxime ethers

In a wide search program toward new and efficient antimicrobial agents, a series of substituted piperidin-4-one oxime ethers (5a-5k) was synthesized and tested for their in vitro antibacterial and antifungal activities. Also, the structures of these oxime ethers and their relative stereochemistries have been investigated by nuclear magnetic resonance spectroscopy. In all the oxime ethers synthesized, the orientation of the N-O bond of the oxime ether moiety syn to C-5 (E-isomer) was deduced based on 1H NMR and 13C NMR spectra. It was found that the sterically less hindered compounds, either C-3 (H) and C-5 (H)- or C-3 (Me) and C-5 (H) -substituted ones 5a, 5c, 5d, 5f, 5g, 5i and 5j prefer chair conformation, whereas the sterically more hindered C-3 (Me) and C-5 (Me) -substituted ones 5b, 5e, 5h, and 5k prefer twist-boat conformation. Among the oxime ethers tested, 1,3,5-trimethyl-2,6-diphenylpiperidin-4-one O-(2-chlorophenylmethyl)oxime (5h) exhibited good antibacterial property against Bacillus subtilis, with minimum inhibitory concentration (MIC) closer to that of reference drug, streptomycin. Compounds, 1,3-dimethyl-2,6-diphenylpiperidin-4-one O-(2-chlorophenylmethyl)oxime (5g) and 1,3-dimethyl-2,6-diphenylpiperidin-4-one O-(2-bromophenylmethyl)oxime (5j) showed potent antifungal activity against Aspergillus flavus and Candida-51, respectively. The later compound 5j is more active than the reference drug while the activity of the former one 5g is similar to that of the reference drug, amphotericin B in terms of MIC. The present results may be used as key steps for the construction of novel chemical entities with better pharmacological profiles than standard drugs.

Reactivities of Variously Substituted 4-Heteracyclohexanones in the Formation of Oximes

The rates of oxime formation of 41 heterocyclic ketones have been measured at 5 deg C in aqueous alcoholic solution buffered at pH 6.85.The data indicate an overall second-order reaction, first order each in ketone and hydroxylamine.In all cases investiga