悉尼酮
悉尼酮是一類含有第5位置有酮基的1,2,3-噁二唑的介离子杂环化合物。 [1][2][3] 跟其他介離子化合物一樣，它們具有雙極性。它們擁有正電荷和負電荷，在環上離域。根據近期[何时？]的電腦計算，悉尼酮和其他類似的介離子化合物不具有芳香性，「卻通過電子和電荷離域在兩個不同的區域裡有良好的穩定性」。[4]悉尼酮的名稱來自悉尼。
| 悉尼酮 | |
|---|---|
| |
| IUPAC名 2H-Oxadiazol-5-one | |
| 别名 | 1,2,3-Oxadiazol-5(2H)-one |
| 识别 | |
| CAS号 | 534-24-7 
|
| PubChem | 12443168 |
| ChemSpider | 65792731 |
| SMILES |
|
| 性质 | |
| 化学式 | C2H2N2O2 |
| 摩尔质量 | 86.05 g·mol−1 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
悉尼酮的酮基（=O）被亚胺基（=NH）取代，形成悉尼酮亚胺。它們出現於興奮劑feprosidnine和美索卡的子結構裡。
發現 编辑
悉尼酮首次由Earl和Mackney於1935年製備，通過用乙酸酐將N-亞硝基-N-苯甘胺酸脫水環化製造。[5]後期工作表明這個方法通常可以應用於N-取代的氨基酸的亚硝胺。[2]
化學結構 编辑
參見 编辑
參考文獻 编辑
- ^ 國際純化學和應用化學聯合會，化學術語概略，第二版。（金皮書）(1997)。在線校正版: (2006–) "sydnones"。doi:10.1351/goldbook.S05990
- ^ 2.0 2.1 Stewart, F. H. C. The Chemistry of the Sydnones. Chemical Reviews. 1 April 1964, 64 (2): 129–147. doi:10.1021/cr60228a004.
- ^ Browne, Duncan L.; Harrity, Joseph P.A. Recent developments in the chemistry of sydnones. Tetrahedron. January 2010, 66 (3): 553–568. doi:10.1016/j.tet.2009.10.085.
- ^ Simas, Alfredo. Are mesoionic compounds aromatic?. Canadian Journal of Chemistry. 1998, 76: 869–872. doi:10.1139/v98-065.
- ^ Earl, J. Campbell; Mackney, Alan W. 204. The action of acetic anhydride on N-nitrosophenylglycine and some of its derivatives. Journal of the Chemical Society (Resumed). 1935: 899. doi:10.1039/jr9350000899.
- S. Wiechmann; T. Freese; M. H. H. Drafz; E. G. Hübner; J. C. Namyslo; M. Nieger; A. Schmidt. Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses.. Chem. Commun. 2014, 50: 11822–11824. doi:10.1039/C4CC05461J
. - Claude V. Greco; Wayne H. Nyberg; C. C. Cheng . Synthesis of Sydnones and Sydnone Imines. Journal of Medicinal Chemistry. 1962, 5 (4): 861–865. doi:10.1021/jm01239a022.
- Wilson Baker; W. D. Ollis. Meso-ionic compounds. Quarterly Reviews, Chemical Society. 1957, 11: 15–30. doi:10.1039/QR9571100015.
- Joseph Fugger; Jack M. Tien; I. Moyer Hunsberger . The Preparation of Substituted Hydrazines. I. Alkylhydrazines via Alkylsydnones. J. Am. Chem. Soc. 1955, 77 (7): 1843–1848. doi:10.1021/ja01612a039.
- Jack M. Tien ; I. Moyer Hunsberger . The Preparation of Substituted Hydrazines. II.1 3-Pyridylhydrazine via the Phototropic N-(3-Pyridyl)-sydnone. J. Am. Chem. Soc. 1955, 77 (24): 6604–6607. doi:10.1021/ja01629a052. 88, 178 (1961);
- Jack M. Tien ; I. Moyer Hunsberger . Sydnones. III. Preparation and Interconversion of Mercurated Derivatives of N-(3-Pyridyl)-sydnone1-3a. J. Am. Chem. Soc. 1961, 83 (1): 178–182. doi:10.1021/ja01462a035.
- Alan R. Katritzky. Chem. Ind. . 1955: 521 . 缺少或
|title=为空 (帮助) - Alexander Lawson ; D. H. Miles . Some new mesoionic compounds. J. Chem. Soc. . 1959: 2865–2871. doi:10.1039/JR9590002865.
- J. Ogilvie; V. K. Miyamoto; Thomas C. Bruice. A Kinetic Study of the Reaction of a "Meso-ionic" Compound (Dehydrodithizone) with Haloacetates. J. Am. Chem. Soc. 1961, 83 (11): 2493–2495. doi:10.1021/ja01472a017.
- LEMONT B. KIER, LAURETTA E. FOX, D. DHAWAN & I. W. WATERS. A New Class of Central Nervous System Stimulants. Nature. 1962, 195 (4843): 817–818. Bibcode:1962Natur.195..817K. PMID 14455827. doi:10.1038/195817a0.
