516031

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate

96%

• Synonyme(s) : (2S)-1,2-Aziridinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester, (S)-N-Cbz-aziridine-2-carboxylic acid methyl ester, 1-Benzyl 2-methyl (S)-(−)-1,2-aziridinedicarboxylate, Methyl (S)-N-Cbz-aziridine-2-carboxylate
• Formule empirique (notation de Hill): C₁₂H₁₃NO₄
• Numéro CAS: 104597-98-0
• Poids moléculaire : 235.24
• Numéro MDL: MFCD06799020
• Code UNSPSC : 12352005
• ID de substance PubChem : 24873860
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: 96%
• Activité optique: [α]20/D −25°, c = 1 in toluene
• Indice de réfraction: n20/D 1.519 (lit.)
• Point d'ébullition: 160-165 °C/2 mmHg (lit.)
• Densité: 1.19 g/mL at 25 °C (lit.)
• Groupe fonctionnel: ester; phenyl
• Chaîne SMILES: COC(=O)C1CN1C(=O)OCc2ccccc2
• InChI: 1S/C12H13NO4/c1-16-11(14)10-7-13(10)12(15)17-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3/t10-,13?/m0/s1
• Clé InChI: GTZJUBQWCWZING-NKUHCKNESA-N

Description

Description générale

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate is commonly used as an electrophilic aziridination reagent in organic synthesis. It is a chiral bicyclic lactam reagent that can be used for the synthesis of chiral aziridines from alkenes. The reagent is particularly useful in the synthesis of chiral building blocks.

Application

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate can be used as a reactant in the total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid. It is also used in the preparation of optically active aziridine derivatives.

Informations sur la sécurité

• Code de la classe de stockage: 10 - Combustible liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves