50586-10-2

Basic information

• Product Name: 1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE
• Synonyms: 1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE
• CAS NO: 50586-10-2
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.26
• Mol File: 50586-10-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE(50586-10-2)
• EPA Substance Registry System: 1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE(50586-10-2)

Safety Data

• Hazardous Substances Data: 50586-10-2(Hazardous Substances Data)

Usage

General Description

1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE, also known as MBMP, is a chemical compound commonly used in the synthesis of pharmaceuticals and agrochemicals. It is a cyclic amine derivative with a piperidin-2-one core structure, and its benzyl group gives it stability and reactivity. MBMP has been found to exhibit anti-inflammatory and analgesic properties, making it a valuable chemical for drug development. Additionally, it is used as a key intermediate in the production of a variety of pharmaceuticals and agrochemicals due to its versatile reactivity and functional group tolerance. Keywords: MBMP, 1-BENZYL-3-METHYLENE-PIPERIDIN-2-ONE, chemical compound, pharmaceuticals, agrochemicals, synthesis, cyclic amine derivative, piperidin-2-one, anti-inflammatory, analgesic, drug development, intermediate, reactivity, functional group tolerance.

Upstream product

• 100-39-0 benzyl bromide 
• 72551-53-2 ethyl 1-benzylpiperidine-3-carboxylate 
• 71962-74-8 Ethyl nipecotate 
• 4783-65-7 N-benzyl-2-piperidinone 
• 86954-08-7 N-benzyl-4-bromo-4-pentenamide 
• 86953-48-2 4-bromo-pent-4-enoic acid 
• 86953-47-1 Diethyl 2-(2-bromo-2-propenyl)malonate 
• 35804-44-5 ethyl 4-bromo-4-pentenoate 
• 201230-82-2 carbon monoxide 
• 157286-98-1 N-benzyl-4-<(trifluoromethanesulfonyl)oxy>-4-pentenylamine 
• 86953-49-3 N-benzyl-4-bromo-4-pentenylamine 

Downstream Products

• 37672-46-1 3-methyl-1-(phenylmethyl)-2-piperidinone 

Relevant articles and documents

Systematic Investigation into the Matsuda-Heck Reaction of α-Methylene Lactones: How Conformational Constraints Direct the β-H-Elimination Step

α-Methylene-γ-butyrolactone and α-methylene-δ-valerolactone undergo Pd-catalyzed Matsuda-Heck couplings with arene diazonium salts to α-benzyl butenolides or pentenolides, respectively, or to α-benzylidene lactones. The observed regioselectivity is strongly ring size dependent, with six-membered rings giving exclusively α-benzyl pentenolides, whereas the five-membered α-methylene lactone reacts to mixtures of regioisomers with a high proportion of (E)-α-benzylidene-γ-butyrolactones. DFT calculations suggest that the reasons for these differences are not thermodynamic but kinetic in nature. The relative energies of the conformers of the Pd σ-complexes resulting from insertion into the Pd-aryl bond were correlated with the dihedral angles between Pd and endo-β-H. This correlation revealed that in the case of the six-membered lactone an energetically favorable conformer adopts a nearly synperiplanar Pd/endo-β-H arrangement, whereas for the analogous Pd σ-complex of the five-membered lactone the smallest Pd/endo-β-H dihedral angle is observed for a conformer with a comparatively high potential energy. The optimized conditions for Matsuda-Heck arylations of exo-methylene lactones were eventually applied to the synthesis of the natural product anemarcoumarin A.

Synthesis of α,β-unsaturated lactams by palladium-catalysed intramolecular carbonylative coupling

Amino vinyl triflates have been shown to undergo an intramolecular, carbonylative coupling in the presence of a palladium catalyst to afford α,β-unsaturated lactams.

AMINO ACID DERIVATIVES

New substituted acyl derivatives of amino acids which have the general formula STR1 are useful as angiotensin converting enzyme inhibitors.