118987-40-9

Basic information

• Product Name: 2-Azetidinone, 3-acetyl-1,3-dimethyl-4-methylene- (9CI)
• Synonyms: 2-Azetidinone, 3-acetyl-1,3-dimethyl-4-methylene- (9CI)
• CAS NO: 118987-40-9
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.17844
• Product Categories: ACETYLGROUP
• Mol File: 118987-40-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Azetidinone, 3-acetyl-1,3-dimethyl-4-methylene- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-acetyl-1,3-dimethyl-4-methylene- (9CI)(118987-40-9)
• EPA Substance Registry System: 2-Azetidinone, 3-acetyl-1,3-dimethyl-4-methylene- (9CI)(118987-40-9)

Safety Data

• Hazardous Substances Data: 118987-40-9(Hazardous Substances Data)

Usage

Family

Azetidinone

Classification

Beta-lactam
Contains a four-membered ring with a nitrogen atom
Widely used as an intermediate in pharmaceutical and organic compound synthesis
Useful building block for the synthesis of bioactive molecules, including antibiotics, antivirals, and other pharmaceuticals
Exhibits potential antimicrobial and antitumor activities
Valuable chemical intermediate with diverse applications in pharmaceutical and chemical industries

Upstream product

• 86421-68-3 2,3,5,6-tetramethylpyrimidin-4-(3H)-one 

Relevant articles and documents

Photochemistry of 5-methylpyrimidin-4-ones in acetic acid solution: Thermal rearrangements of Dewar pyrimidinones and 4-acetoxyazetidin-2-ones

Irradiation of 3,6-dialkyl-5-methylpyrimidin-4-ones (1a-f) in acetic acid-acetonitrile (1:2, v/v) solution at 0 °C gave 4-acetoxy-3-(1-imino-2,2- dimethylpropyl)-1,3,4-trimethylazetidin-2-one (3a), 6-acetoxy-7-(1-imino-2,2- dimethylpropyl)-7-methyl-1-azabicyclo[4.2.0]octan-8-one (3b), 4-acetoxy-3-acetyl-1,3,4-trialkylazetidin-2-ones (4c-e), 4-acetoxy-3-acetyl-1,3- dimethylazetidin-2-one (4f), 3-acetyl-4-alkylidene-1,3-dimethylazetidin-2-ones (5d) and (5e) as the major products. Reaction of 1,4,6-trimethyl-3-t-butyl-2,6- diazabicyclo[2.2.0]hex-2-en-5-one (2a) (Dewar pyrimidinone) in acetic acid-acetonitrile (1:14, v/v) solution at 0 °C and thermolysis of (2a) without solvent at 80 °C gave the imine azetidin-2-one (3a) and 2,3,5-trimethyl-6-t-butylpyrimidin-4(3H)-one (1a) respectively as the major products. Reactions of the imino azetidin-2-ones (3a) and (3b) and the 4-acetoxyazetidin-2-ones (4c-e) in the presence of acetic acid at 21-40 °C and without solvent at 100-110 °C were carried out to elucidate the rearrangements. The major products from (3a) and (3b) in acidic solutions at 40 °C were N-acetyl-3-acetamido-2,4,4,N-tetramethylpent-2-enamide (6a), N-methylacetamide (9a), 2,5-dimethyl-4-t-butyl-1,3-oxazin-6-one (10a), 2-piperidone (9b), and 1,3-oxazin-6-one (10b) = (10a), and from the thermolysis of (3a) and (3b) at 100-110 °C were the pyrimidin-4-ones (1a) and (1b), 1,3-dimethyl-3-pivaloyl-4-vinylazetidin-2-one (5a) and 7-methyl-7-pivaloyl-1- azabicyclo[4.2.0]octa-5-en-8-one (5b). Both reactions of (4d,e) at 23-24 °C in acidic solutions and of (4c,d) without solvent at 100-110 °C gave the 3-acetyl-4-alkylidene-1,3-dimethylazetidin-2-ones (5c-e) as the major products. The reaction mechanisms and intermediates of these reactions are discussed.