516031

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

96%

• Sinónimos: (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
• Fórmula empírica (notación de Hill): C₁₂H₁₃NO₄
• Número de CAS: 104597-98-0
• Peso molecular: 235.24
• Número MDL: MFCD06799020
• Código UNSPSC: 12352005
• ID de la sustancia en PubChem: 24873860
• NACRES: NA.22

Propiedades

• Ensayo: 96%
• actividad óptica: [α]20/D −25°, c = 1 in toluene
• índice de refracción: n20/D 1.519 (lit.)
• bp: 160-165 °C/2 mmHg (lit.)
• densidad: 1.19 g/mL at 25 °C (lit.)
• grupo funcional: ester; phenyl
• cadena 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
• Clave InChI: GTZJUBQWCWZING-NKUHCKNESA-N

Descripción

Descripción general

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.

Aplicación

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.

Información de seguridad

• Código de clase de almacenamiento: 10 - Combustible liquids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves