悉尼酮是一类含有第5位置有基的1,2,3-𫫇二唑英语oxadiazole介离子英语mesoionic杂环化合物。 [1][2][3] 跟其他介离子化合物一样,它们具有双极性。它们拥有正电荷和负电荷,在环上离域。根据近期[何时?]的电脑计算,悉尼酮和其他类似的介离子化合物不具有芳香性,“却通过电子和电荷离域在两个不同的区域里有良好的稳定性”。[4]悉尼酮的名称来自悉尼

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  checkY
PubChem 12443168
ChemSpider 65792731
SMILES
 
  • C1=NNOC1=O
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(=O)被亚胺基(=NH)取代,形成悉尼酮亚胺英语sydnone imine。它们出现于兴奋剂feprosidnine英语feprosidnine美索卡英语mesocarb的子结构里。

发现

悉尼酮首次由Earl和Mackney于1935年制备,通过用乙酸酐将N-亚硝基-N-苯甘胺酸脱水环化制造。[5]后期工作表明这个方法通常可以应用于N-取代的氨基酸亚硝胺[2]

化学结构

 

参见

参考文献

  1. ^ 国际纯化学和应用化学联合会化学术语概略,第二版。(金皮书)(1997)。在线校正版: (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=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. 

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