516031

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

96%

• Sinônimo(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
• Fórmula empírica (Notação de Hill): C₁₂H₁₃NO₄
• Número CAS: 104597-98-0
• Peso molecular: 235.24
• Número MDL: MFCD06799020
• Código UNSPSC: 12352005
• ID de substância PubChem: 24873860
• NACRES: NA.22

Propriedades

• Ensaio: 96%
• atividade óptica: [α]20/D −25°, c = 1 in toluene
• índice de refração: n20/D 1.519 (lit.)
• p.e.: 160-165 °C/2 mmHg (lit.)
• densidade: 1.19 g/mL at 25 °C (lit.)
• grupo funcional: ester; phenyl
• cadeia de caracteres 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
• chave InChI: GTZJUBQWCWZING-NKUHCKNESA-N

Descrição

Descrição geral

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.

Aplicação

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.

Informações de segurança

• Código de classe de armazenamento: 10 - Combustible liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves