2,5-噁唑烷二酮

甘氨酸N-羧酸酐
別名	2,5-噁唑烷二酮; 噁唑烷-2,5-二酮
識別
CAS號	2185-00-4
PubChem	75136
ChemSpider	67684
SMILES	C1C(=O)OC(=O)N1;
性質
化學式	C3H3NO3
摩爾質量	101.06 g·mol−1
外觀	白色固體
密度	1.74 g/cm3
熔點	96-98 °C（369-371 K）（）
危險性
	GHS危險性符號;
GHS提示詞	Danger
H-術語	H315, H318, H335
P-術語	P261, P264, P264+265, P271, P280, P302+352, P304+340, P305+354+338, P317, P319, P321, P332+317, P362+364, P403+233
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

甘氨酸N-羧酸酐（英語：Glycine N-carboxyanhydride），也叫2,5-噁唑烷二酮（2,5-Oxazolidinedione），是一種有機化合物，化學式為HNCH(CO)₂O。無色固體，是甘氨酸光氣化的產物。^[3]^[4]甘氨酸N-羧酸酐是胺基酸N-羧酸酐中最簡單的成員。它也是2,5-噁唑烷二酮雜環家族的母體。

其它衍生物[編輯]

2,5-噁唑烷二酮也可以由胺基酸的席夫鹼衍生物製備。^[5]

參見[編輯]

2,4-噁唑烷二酮，母環存在於多種抗驚厥藥中。

參考資料[編輯]

^ Kanazawa, Hitoshi; Matsuura, Yoshiki; Tanaka, Nobuo; Kakudo, Masao; Komoto, Tadashi; Kawai, Tohru. The Crystal and Molecular Structure ofN-Carboxy Anhydride of Glycine. Bulletin of the Chemical Society of Japan. 1976, 49 (4): 954–956. doi:10.1246/bcsj.49.954.
^ Wilder, Renee; Mobashery, Shahriar. The use of triphosgene in preparation of N-carboxy .alpha.-amino acid anhydrides. The Journal of Organic Chemistry. 1992, 57 (9): 2755–2756. doi:10.1021/jo00035a044.
^ Kricheldorf HR. Polypeptides and 100 years of chemistry of alpha-amino acid N-carboxyanhydrides. Angewandte Chemie. September 2006, 45 (35): 5752–84. PMID 16948174. doi:10.1002/anie.200600693.
^ Tian ZY, Zhang Z, Wang S, Lu H. A Moisture-Tolerant Route to Unprotected α/β-Amino Acid N-carboxyanhydrides and Facile Synthesis of Hyperbranched Polypeptides. Nature Communications. October 2021, 12 (1): 5810. Bibcode:2021NatCo..12.5810T. PMC 8490447 . PMID 34608139. doi:10.1038/s41467-021-25689-y.
^ Sucu BO, Ocal N, Erden I. Direct synthesis of imidazolidin-4-ones via cycloadditions of imines with a Leuchs' anyhdride. Tetrahedron Letters. 2015, 56 (20): 2590–2. doi:10.1016/j.tetlet.2015.04.002.

[1] Kanazawa, Hitoshi; Matsuura, Yoshiki; Tanaka, Nobuo; Kakudo, Masao; Komoto, Tadashi; Kawai, Tohru. The Crystal and Molecular Structure ofN-Carboxy Anhydride of Glycine. Bulletin of the Chemical Society of Japan. 1976, 49 (4): 954–956. doi:10.1246/bcsj.49.954.

[2] Wilder, Renee; Mobashery, Shahriar. The use of triphosgene in preparation of N-carboxy .alpha.-amino acid anhydrides. The Journal of Organic Chemistry. 1992, 57 (9): 2755–2756. doi:10.1021/jo00035a044.

[3] Kricheldorf HR. Polypeptides and 100 years of chemistry of alpha-amino acid N-carboxyanhydrides. Angewandte Chemie. September 2006, 45 (35): 5752–84. PMID 16948174. doi:10.1002/anie.200600693.

[Tian-4] Tian ZY, Zhang Z, Wang S, Lu H. A Moisture-Tolerant Route to Unprotected α/β-Amino Acid N-carboxyanhydrides and Facile Synthesis of Hyperbranched Polypeptides. Nature Communications. October 2021, 12 (1): 5810. Bibcode:2021NatCo..12.5810T. PMC 8490447 . PMID 34608139. doi:10.1038/s41467-021-25689-y.

[Sucu_et_al_2015-5] Sucu BO, Ocal N, Erden I. Direct synthesis of imidazolidin-4-ones via cycloadditions of imines with a Leuchs' anyhdride. Tetrahedron Letters. 2015, 56 (20): 2590–2. doi:10.1016/j.tetlet.2015.04.002.

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