25012-72-0

Basic information

• Product Name: 1-Methyl-4-oxopiperidin-3-carboxylic acid ethyl ester
• Synonyms: 1-Methyl-4-oxopiperidin-3-carboxylic acid ethyl ester;Ethyl 1-Methyl-4-oxopiperidine-3-carboxylate;1-Methyl-4-oxo-piperidine-3-carboxylic acid ethyl ester
• CAS NO: 25012-72-0
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.2203
• Mol File: 25012-72-0.mol

Chemical Properties

• Boiling Point: 272℃
• Flash Point: 118℃
• Appearance: /
• Density: 1.101
• Storage Temp.: 2-8°C
• PKA: 10.68±0.20(Predicted)
• CAS DataBase Reference: 1-Methyl-4-oxopiperidin-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-oxopiperidin-3-carboxylic acid ethyl ester(25012-72-0)
• EPA Substance Registry System: 1-Methyl-4-oxopiperidin-3-carboxylic acid ethyl ester(25012-72-0)

Safety Data

• Hazardous Substances Data: 25012-72-0(Hazardous Substances Data)

Upstream product

• 539-74-2 Ethyl 3-bromopropionate 
• 100-46-9 benzylamine 
• 140-88-5 ethyl acrylate 
• 6315-60-2 3,3'-methylimino-di-propionic acid diethyl ester 

Downstream Products

• 111441-23-7 5-methyl-1,2-diphenyl-1,2,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one 
• 1445-73-4 1-Methyl-4-piperidone 
• 37673-66-8 4-hydroxy-1-methyl-piperidine-3-carboxylic acid ethyl ester 
• 52094-69-6 8-methyl-1,3,8-triazaspiro<4.5>decane-2,4-dione 
• 139452-53-2 6-methyl-2-phenyl-5,6,7,8-tetrahydro-3H-pyrido<4,3-d>pyrimidin-4-one 
• 929258-77-5 ethyl 3-(2-bromo-3-methylbenzyl)-N-methyl-4-oxopiperidine-3-carboxylate 
• 26822-37-7 N,N-dimethyl-4-oxopiperidinium iodide 
• 5570-77-4 4-chloro-1-methylpiperidine 
• 106-52-5 N-methyl-4-hydroxypiperidine 
• 52835-63-9 (3E,5E)-3,5-dibenzylidene-1-methylpiperidin-4-one 
• 97762-23-7 4-diphenyl acetoxy N-methyl piperidine 
• 67288-79-3 3,5-bis-(2-chloro-benzylidene)-1-methyl-piperidin-4-one 
• 2167-01-3 1-methyl-3,5-bis-[1]naphthylmethylene-piperidin-4-one 
• 52835-56-0 (+/-)-6-((E)-benzylidene)-2,8-dimethyl-10t-phenyl-(10at)-1,2,3,4,6,7,8,9,10,10a-decahydro-pyrano[3,2-c;5,6-c']dipyridin-4ar-ol 

Relevant articles and documents

Titanium mediated cyclization of N-substituted di(β-carbethoxyethyl)amines: Preparation of 1-substituted-3-carbethoxy-4-piperidones

Dieckmann cyclisation of N-substituted di(β-carbethoxyethyl)amines with titanium tetrachloride in DCM in the presence of triethylamine leads to the formation of 3-carbethoxy-4-piperidones.

Synthesis and antiproliferative activity of cyclic arylidene ketones: a direct comparison of monobenzylidene and dibenzylidene derivatives

Abstract To give further insight into the influence of the structural modifications of enones and dienones on their antiproliferative properties, 25 derivatives of enones: (E)-2-benzylidene-1-cyclohexanones, (E)-2-benzylidene-1-tetralones, (E)-2-benzylidene-1-indanone, and dienones: (E,E)-2,5- or 2,6-dibenzylidene-1-cyclanones, (E,E)-3,5-dibenzylidene-4-piperidones were synthesized using a newly developed "one-pot" synthetic method. Due to the fact that all of them have the same aryl substituents (phenyl or 4-chlorophenyl) in the arylidene moiety, it is possible to compare the relevant contribution of the single-point structural modifications (type of ring or N-substitution) on their potency on the basis of their IC 50 values. Their antiproliferative activity was evaluated against the following four human adherent cancer cell lines: HeLa, A431, A2780, and MCF7. The cytotoxicity screen has revealed that the dibenzylidene dienones in general dominate the monobenzylidene enones in this respect. The nitrogen-containing heterocyclic dienones at the same time displayed higher inhibitory properties toward these human carcinoma cell lines compared with their homocyclic dienone analogs. One of the eight newly prepared 4-piperidone derivatives, N-(γ-oxobutyl)-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone is as potent a cell growth inhibitor (IC 50 of 0.438-1.409 μM) as the N-methyl-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone (IC 50 of 0.447-1.048 μM), one of the most active among the previously described compounds in this series. Catalytic hydrogen-transfer isomerization of compounds with two exocyclic benzylidene double bonds to derivatives with endocyclic double bonds results in the complete loss of antiproliferative activity. The structural modifications and 50 % inhibitory concentration (IC 50) values resulted in correlations which can promote the design of more potent derivatives of the 4-piperidone dienones.