3883-34-9

Basic information

• Product Name: C₂₂H₂₃NO
• Synonyms: C₂₂H₂₃NO
• CAS NO: 3883-34-9
• Molecular Weight: 317.431
• Mol File: 3883-34-9.mol

Chemical Properties

• CAS DataBase Reference: C₂₂H₂₃NO(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₂H₂₃NO(3883-34-9)
• EPA Substance Registry System: C₂₂H₂₃NO(3883-34-9)

Safety Data

• Hazardous Substances Data: 3883-34-9(Hazardous Substances Data)

Upstream product

• 1445-73-4 1-Methyl-4-piperidone 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 102756-58-1 1-methyl-3,5-bis-(4-methyl-benzyl)-1H-pyridin-4-one 

Relevant articles and documents

Synthesis and molecular modeling studies of indole-based antitumor agents

Indole-based compounds 30-63 were synthesized by the multi-component 1,3-dipolar cycloaddition reaction of 1-alkyl-3,5-bis(arylidene)-4-piperidones 11-25 with azomethine ylides (generated by the condensation of isatins 26-28 with sarcosine 29). The single crystal X-ray studies of 46 and 48 supported the regio- and stereoselectivity of the reaction. Most of the synthesized spiro-indoles exhibited potent antitumor properties against the HeLa (cervical cancer) cell line through in vitro sulfo-rhodamine-B bioassay, higher than that of cisplatin. Only compound 54 showed bio-potency against the HepG2 (hepatocellular cancer) cell line, comparable to that of doxorubicin hydrochloride (standard reference). 3D-Pharmacophore and 2D-QSAR studies were used to validate the observed biological data and determine the most important parameters controlling activity. The estimated bio-properties from the computational studies showed high approximations to the experimental data.

Amino functionalized mesoporous silica decorated with iron oxide nanoparticles as a magnetically recoverable nanoreactor for the synthesis of a new series of 2,4-diphenylpyrido[4,3-d]pyrimidines

(Fe2O3)-MCM-41-nPrNH2 as a magnetically recoverable nanoreactor, was prepared through the reaction of (Fe 2O3)-MCM-41 with 3-aminopropyltriethoxysilane in refluxing dry toluene. The catalyst with 10 wt% of loaded iron oxide nanoparticles was found to be a highly efficient nanocatalyst for the synthesis of a new class of 2,4-diphenylpyrido[4,3-d]pyrimidines under solvent free conditions in high to quantitative yields. By using an external magnet the catalyst was recovered and reused several times without any loss of efficiency. The prepared catalyst was characterized by transmission electron microscopy (TEM), Fourier transform infrared (FT-IR) spectroscopy, X-ray powder diffraction (XRD), and nitrogen physisorption measurements.

Microwave accelerated facile and efficient synthesis of piperido[3′,4′:5,6]pyrano[2,3-d] pyrimidinones catalyzed by basic ionic liquid [BMIM]OH

A basic ionic liquid [BMIM]OH could very efficiently catalyze the synthesis of piperido[3′,4′:5,6]pyrano[2,3-d]pyrimidinone derivatives from pyrano[3,2-c]piperidine analogues and carbonyl compounds. [BMIM]OH acted as a catalyst as well as the reaction medium and could be used for the reactions for five times without any appreciable loss of its catalytic efficiency. The synergic couple of microwave and ionic liquid provided high yields of the product in very short reaction times and allowed easy workup.

Microwave-assisted synthesis of pyrimido[4,5-b][1,6]naphthyridin-4(3H)-ones with potential antitumor activity

The 6,7,8,9-tetrahydropyrimido[4,5-b][1,6]naphthyridin-4(3H,5H,10H)-ones 4,5a-g and their oxidized forms 6,7a-g were obtained from the catalyst-free reaction of 6-amino-2-methylthiopyrimidin-4(3H)-one 3 and (E)-3,5- bis(benzylidene)-1-alkyl-4-piperidones

Magnetic graphene oxide anchored sulfonic acid as a novel nanocatalyst for the synthesis of N-aryl-2-amino-1,6-naphthyridines

Magnetic graphene oxide functionalized with sulfonic acid (Fe 3O4-GO-SO3H) was used as a new recyclable nanocatalyst for one-pot synthesis of N-aryl-2-amino-1,6-naphthyridine derivatives under solvent free conditions. The catalyst could be easily recovered from the reaction mixture by an external magnet and reused without significant decrease in activity even after 4 runs. This nanocatalyst exhibited better activities to other commercially available sulfonic acid catalysts.

Application of MCM-41-SO3H as an advanced nanocatalyst for the solvent free synthesis of pyrano[3,2-c]pyridine derivatives

MCM-41-SO3H, an ordered mesoporous silica material in which MCM-41 with covalently anchored sulfonic acid groups was used as an acidic catalyst for the rapid and 'green' synthesis of pyrano[3,2-c]pyridine derivatives under solvent-free conditions. Reusability of the catalyst, high yields, short reaction times, simplicity and easy workup are advantages of this novel synthetic procedure compared to the conventional methods reported in the literature.

A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents

The 1,3-dipolar cycloaddition of azomethine ylides derived from substituted isatins and 1,3-thiazolane-4-carboxylic acid to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]-tetrahydro-4(1H)-pyridinones afforded novel spiro-pyrrolothiazoles chemo-, regio- and stereoselectively in quantitative yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB) using agar dilution method. Among the synthesized compounds, spiro[5.3′′]-5′′-nitrooxindole-spiro-[6.3′]-1′-methyl-5′-(2,4-di-chlorophenylmethylidene)tetrahydro-4′(1H)-pyridinone-7-(2,4-dichlorophenyl)tetra-hydro-1H-pyrrolo[1,2-c][1,3]thiazole (9k) was found to be the most active with a minimum inhibitory concentration (MIC) of 0.6 μM against MTB and MDR-TB.

The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones

This study demonstrated that replacement of the axial protons on the C2 and C6 atoms of various 1-methyl-3,5-bis(benzylidene)-4-piperidones 3 by a dimethylene bridge leading to series 2 lowered cytotoxic potencies. Four compounds 2a and 3a-c emerged as lead molecules based on their toxicity towards different neoplasms and their selective toxicity for malignant rather than normal cells. Some possible reasons for the disparity between the IC50 values in the two series of compounds are presented based on molecular modeling, log P values and respiration in rat liver mitochondria.

An efficient method for synthesis of pyrano[3,2-c]pyridine derivatives under microwave irradiation

(Chemical Equation Presented) A series of pyrano[3,2-c]pyridine derivatives were synthesized via reactions of 3,5-dibenzylidenepiperidin-4-one and malononitrile in N,N-dimethylformamide under microwave irradiation. It is a simple, efficient, and promising

An efficient and chemoselective synthesis of 1,6-naphthyridines and pyrano[3,2-c]pyridines under microwave irradiation

A series of 1,6-naphthyridines and pyrano[3,2-c]pyridines were selectively synthesized via microwave-assisted reactions controlled by the nature of the solvent. This has resulted in an efficient and promising synthetic method for constructing the 1,6-naph