4-Acetoxy-2-azetidinone

Base Information

• Chemical Name: 4-Acetoxy-2-azetidinone
• CAS No.: 28562-53-0
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 2933790090
• European Community (EC) Number: 249-083-7
• DSSTox Substance ID: DTXSID20951247
• Nikkaji Number: J250.737D
• Wikidata: Q17122082
• ChEMBL ID: CHEMBL122408
• Mol file: 28562-53-0.mol

Synonyms:4-acetoxy-2-azetidinone

Chemical Property of 4-Acetoxy-2-azetidinone

Chemical Property:

• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: 38-40 °C(lit.)
• Refractive Index: 1.476
• Boiling Point: 296.45 °C at 760 mmHg
• PKA: 13.41±0.40(Predicted)
• Flash Point: 133.089 °C
• PSA: 55.40000
• Density: 1.269 g/cm³
• LogP: -0.27570
• Storage Temp.: 2-8°C
• Solubility.: formic acid: soluble50mg/mL, clear, yellow-orange
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 154

Purity/Quality:

99%, ^*data from raw suppliers

4-Acetoxy-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(=O)N1
• Uses: 4-Acetoxy-2-azetidinone was used in the synthesis of derivatized cyclopentenes in high regio- and diastereoselectivity. It was also used as a heterocyclic synthon for antibiotic and anti-inflammatory agents.

Technology Process of 4-Acetoxy-2-azetidinone

There total 16 articles about 4-Acetoxy-2-azetidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-azetidinone (930-21-2) + peracetic acid (79-21-0) → 4-acetoxy azetidinone (28562-53-0)

Guidance literature:

With Ru-carbon; sodium acetate; acetic acid; In ethyl acetate; for 2.5h; Ambient temperature;

DOI:10.1021/ja00177a067

Reference yield: 89.0%

4-Trimethylsilylazetidin-2-one (80395-83-1) + acetic acid (64-19-7,77671-22-8) → 4-acetoxy azetidinone (28562-53-0)

Guidance literature:

With tetraethylammonium tosylate; In acetonitrile; Ambient temperature; constant current electrolysis;

Reference yield: 88.0%

2-azetidinone (930-21-2) + acetic acid (64-19-7,77671-22-8) → 4-acetoxy azetidinone (28562-53-0)

Guidance literature:

With oxygen; sodium acetate; acetaldehyde; ruthenium trichloride; In ethyl acetate; at 40 ℃;

DOI:10.1016/S0040-4039(00)79446-9

upstream raw materials:

2-azetidinone

peracetic acid

acetic acid

vinyl acetate

Downstream raw materials:

4-phenylcarbonylmethyl-2-azetidinone

ethyl 3-methyl-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

2-acetoxy-acetoacetic acid ethyl ester

4-(2-Oxo-cyclohexyl)-azetidin-2-one

Refernces

• 1、 Lee, Sang Hyup. "Studies on the design and synthesis of new monocyclic β-lactams containing substructures of penicillin G". . p. 2990 - 2994. Retrieved 2014/12/10.
• 2、 Lee, Sang Hyup. "Design and synthesis of new 4-alkylthio monocyclic β-lactams". . p. 121 - 127. Retrieved 2013/08/24.