悉尼酮是一類含有第5位置有基的1,2,3-噁二唑英語oxadiazole介離子英語mesoionic雜環化合物。 [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[何時?]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裏有良好的穩定性」。[4]悉尼酮的名稱來自悉尼

悉尼酮
IUPAC名
2H-Oxadiazol-5-one
別名 1,2,3-Oxadiazol-5(2H)-one
識別
CAS號 534-24-7  checkY
PubChem 12443168
ChemSpider 65792731
SMILES
 
  • C1=NNOC1=O
性質
化學式 C2H2N2O2
摩爾質量 86.05 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

悉尼酮的(=O)被亞胺基(=NH)取代,形成悉尼酮亞胺英語sydnone imine。它們出現於興奮劑feprosidnine英語feprosidnine美索卡英語mesocarb的子結構裏。

發現

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-取代的氨基酸亞硝胺[2]

化學結構

 

參見

參考文獻

  1. ^ 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. ^ 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. 
  3. ^ 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. 
  4. ^ Simas, Alfredo. Are mesoionic compounds aromatic?. Canadian Journal of Chemistry. 1998, 76: 869–872. doi:10.1139/v98-065. 
  5. ^ 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=為空 (幫助)
  • 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. 

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