Grundinformationen
- Standard-SMILES
O=C1CCCC(=O)N1- InChIKey
KNCYXPMJDCCGSJ-UHFFFAOYSA-N- Summenformel
- C5H7NO2
- Durchschnittliche Molmasse
- 113,11 g/mol
- Monoisotopische Masse
- 113,04767846
Überblick
Piperidine-2,6-dione is a dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6. It is a dicarboximide and a member of piperidones.
Namen und Bezeichner
- Bevorzugter Name
- Glutarimide
- IUPAC
- piperidine-2,6-dione
- Lokaler Name
- Glutarimid
- Englischer Name
- Glutarimide
- Summenformel
- C5H7NO2
- Molmasse
- 113.11
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
1121-89-7- PubChem CID
- 70726
- DTXSID
DTXSID7074452- ChEMBL
CHEMBL3763941- ChEBI
CHEBI:5435- UNII
- MV728O9612
- EC Number
- 214-340-4
- Nikkaji
- J137.949F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 46,2 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 116
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 155 · 155-157 °C (lit.)
- Siedepunkt
- 211.82 °C · 211.82°C (rough estimate)
- Dichte
- 1.2416 · 1.2416 (rough estimate)
- Brechungsindex
- 1.42 · 1.4200 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- soluble in Chloroform, DCM
- Aggregatzustand
- Crystals or Crystalline Flakes
- pka
- 11.4 · pKa 11.4 (Uncertain)
- Farbe
- White
- Wasserlöslichkeit
- Soluble in water, hot ethanol and boiling benzene. Insoluble in ether.
- BRN
- 110052 · 110052
- InChI
- InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
- InChIKey
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N
- SMILES
- N1C(=O)CCCC1=O
- CAS Datenbank
- 1121 · 1121-89-7(CAS DataBase Reference)
- EPA chemische Informationen
- Glutarimide (1121-89-7)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/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.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29251995
- RTECS-Nr.
- MA4000000
- risk_code
- 36
- hazard_code
- Xi
- safety_code
- 37/39-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Anwendungen
VerwendenGlutarimide acts as an inhibitor of protein synthesis. Further, it is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. It is also employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids and alfa-fluoro-alfa amino amides. In addition to this, it is used in intramolecular amidocyclopropanation reactions.
Darstellung
synthetischeTo a flask containing 70 gm (0.53 mole) of glutaric acid is added 150 ml (2.2 mole) of 28% aqueous ammonia. The mixture is set for distillation and heated for 7 hr as the temperature of the mixture rises from 90° to 180°C. The temperature is held at 170-180°C for \\ hr or until the evolution of ammonia ceases. The reaction mixture solidifies on cooling and the product is recrystallized from acetone to afford 37.4 gm (63%), m.p. 145-146°C. t may be advantageous to preform the ammonium salt of dicarboxylic acids prior to the application of enough heat to form the imide. The preparation of succinimide is a case in point.
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Ergänzende Hinweise
DefinitionChEBI: Glutarimide (Piperidine-2,6-dione) is a dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6. It is a member of piperidones and a dicarboximide.
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