HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
4-Oxoazetidine-2-carboxylic acid
4-Carboxyazetidin-2-one · 4-Oxoazetidine-2-carboxylic acid · 2-Azetidinecarboxylic acid, 4-oxo- · (2R)-2-azetidinone-4-carboxylic acid
Identifikatoren & physikalische Daten
| CAS No. | 98019-65-9 |
|---|---|
| Summenformel | C4H5NO3 |
| Durchschnittliche Molmasse | 115,09 g/mol |
| Monoisotopische Masse | 115,02694302 g/mol |
| SMILES | O=C1CC(C(=O)O)N1 |
| InChIKey | YSPMLLKKKHCTBN-UHFFFAOYSA-N |
| PubChem CID | 3488064 |
| EC No. | 869-806-5 |
| DTXSID | DTXSID80392950 |
Chemische & physikalische Eigenschaften
| XLogP | -1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,4 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 142 |
| Siedepunkt | 489.4±38.0 °C(Predicted) |
| Dichte | 1.519±0.06 g/cm3(Predicted) |
| Lagerbedingungen | under inert gas (nitrogen or Argon) at 2-8°C |
| pKa (Säurekonstante) | 3.19±0.20(Predicted) |
| InChI | InChI=1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8) |
| InChIKey | YSPMLLKKKHCTBN-UHFFFAOYSA-N |
| SMILES | N1C(=O)CC1C(O)=O |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (100%) |
| Gefahrenklasse | IRRITANT |
Anwendungen & Verwendung
Beschreibung
4-Oxoazetidine-2-carboxylic acid may be interpreted as a cyclic mimetic of the amino acid Asp. Due to the high reactivity of the four-membered ring, this molecule can serve as an “electrophilic trap” in reactions with nucleophiles. 4-oxoazetidine-2-carboxylic acid can be used as a building block for developing enzyme inhibitors, particularly protease inhibitors. It undergoes coupling reactions with amino acids and oligopeptide esters. Following desilylation of the amino acid residue and deprotection, free β-lactam peptides are obtained[1].