Chemistry:Methyl 2-acetamidoacrylate
From HandWiki
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| Names | |
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| Preferred IUPAC name
Methyl 2-acetamidoprop-2-enoate | |
| Other names
Methyl 2-(acetylamino)propenoate
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| Identifiers | |
3D model (JSmol)
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| Properties | |
| C6H9NO3 | |
| Molar mass | 143.142 g·mol−1 |
| Appearance | white solid |
| Melting point | 75–76 °C (167–169 °F; 348–349 K) |
| Hazards | |
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Methyl 2-acetamidoacrylate is the organic compound with the formula CH2=C(NHC(O)CH3)CO2CH3. It is the methyl ester of an N-acetylacrylic acid, which in turn is a derivative of the unstable compound dehydroalanine. Acetylation of the amine in the latter compound prevents tautomerization. It is a white solid.
The compound can be prepared from methyl 2-acetamidopropionate (CH3CH(NHC(O)CH3)CO2CH3), i.e. the methyl ester of N-acetylalanine.[1] Methyl 2-acetamidoacrylate undergoes Michael reactions, e.g. by thiolates.[2]
References
- ↑ Kolar, A. J.; Olsen, R. K. (1977). "A Convenient, Large-Scale Preparation of 2-Acetamidoacrylic Acid and Its Methyl Ester". Synthesis 1977 (7): 457–9. doi:10.1055/s-1977-24439.
- ↑ Petracca, R.; Bowen, K. A.; McSweeney, L.; O’Flaherty, S.; Genna, V.; Twamley, B.; Devocelle, M.; Scanlan, E. M. (2019). "Chemoselective Synthesis of N-Terminal Cysteinyl Thioesters via β,γ-C,S Thiol-Michael Addition". Organic Letters 21 (9): 3281–3285. doi:10.1021/acs.orglett.9b01013. PMID 31017793. https://figshare.com/articles/journal_contribution/22787930.
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