3-亚硝基-1,3-恶唑烷-2-酮 | 38347-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-亚硝基-1,3-恶唑烷-2-酮
• 英文名称: 3-Nitrosooxazolidin-2-one
• 英文别名: 3-nitroso-2-oxazolidinone；3-nitroso-2-oxazolidone；3-nitroso-oxazolidin-2-one；3-Nitroso-oxazolidin-2-on；3-nitroso-1,3-oxazolidin-2-one
• CAS: 38347-74-9
• 化学式: C₃H₄N₂O₃
• 分子量: 116.076
• InChiKey: MDACSTFMCAQQET-UHFFFAOYSA-N

物化性质

• 熔点：
  50-53 °C
• 沸点：
  143.1±23.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-亚硝基-1,3-恶唑烷-2-酮 在 盐酸 作用下， 以 甲醇 为溶剂， 以35%的产率得到2-唑烷酮
  参考文献：
  名称：

  Cyclization of (2-hydroxyethyl)urea derivatives to give 3-nitroso-2-oxazolidinones under usual nitrosation conditions.

  摘要：

  (2-羟乙基)脲衍生物(Ia-e)在酸的存在下与亚硝酸钠反应，或在氯仿中与亚硝基氯反应，得到了3-亚硝基-2-噁唑烷酮(IIa-e)，产率为10-77%。这些3-亚硝基-2-噁唑烷酮在甲醇中与氯化氢脱亚硝，得到相应的2-噁唑烷酮(IIIa-e)，产率为35-60%。一种N,N-二取代脲，即1-(2-羟乙基)-1-甲基脲(If)在相同条件下也环化，生成3-甲基-2-噁唑烷酮(IIf)。文中讨论了这种环化反应的机制。

  DOI：

  10.1248/cpb.33.497
• 作为产物：
  描述：

  (羟基乙基)脲 在 亚硝酰氯 作用下， 以 氯仿 为溶剂， 以42%的产率得到3-亚硝基-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Cyclization of (2-hydroxyethyl)urea derivatives to give 3-nitroso-2-oxazolidinones under usual nitrosation conditions.

  摘要：

  (2-羟乙基)脲衍生物(Ia-e)在酸的存在下与亚硝酸钠反应，或在氯仿中与亚硝基氯反应，得到了3-亚硝基-2-噁唑烷酮(IIa-e)，产率为10-77%。这些3-亚硝基-2-噁唑烷酮在甲醇中与氯化氢脱亚硝，得到相应的2-噁唑烷酮(IIIa-e)，产率为35-60%。一种N,N-二取代脲，即1-(2-羟乙基)-1-甲基脲(If)在相同条件下也环化，生成3-甲基-2-噁唑烷酮(IIf)。文中讨论了这种环化反应的机制。

  DOI：

  10.1248/cpb.33.497

文献信息

• Gas/Solid Reactions with Nitrogen Dioxide
  作者：Gerd Kaupp、Jens Schmeyers

  DOI：10.1021/jo00122a031

  日期：1995.9

  Numerous gas/solid reactions of nitrogen dioxide with organic substrates are investigated preparatively and mechanistically. Gaseous NO2 reacts with crystalline stable free radicals (nitroxyls 1, verdazyl 6) by electron transfer. The nitrite ions formed are irreversibly oxidized by NO2 via oxygen atom transfer. Solid cation nitrates are formed quantitatively. Thione bonds of thiohydantoins 8 are transformed to carbonyl bonds with formation of sulfur and NO presumably via nitrites as intermediates. Hydantoin 13 oxygenates at its free 5-methylene group via C-H abstraction and nitrite or it undergoes N-1 nitration via N-H abstraction depending on the conditions. Both reactions proceed quantitatively. 1,3-Oxazolidin-2-one (15) gives N-nitration and N-nitrosation with the NO produced. Nonenolized crystalline barbituric acids 17 are quantitatively nitrated (C-N bond formation with radicals) at their methylene groups. 4-Hydroxybenzaldehyde (19) and vanilline (22) give quantitative aromatic nitration (C-N bond formation with arenes) without melting. All possible regioisomers are formed. Solid 9-methylanthracene (26) gives a quantitative yield of its 10-nitro derivative 27. Crystalline anthracene (28) and gaseous NO2 yield 3 primary products 29 (cis; trans) and the new dimeric product 30 as well as the stable secondary products 31 and 32. The gas/solid tetranitration of tetraphenylethylene (33) is severely hindered by the water of reaction. However, a 95% yield of pure tetrakis(p-nitrophenyl)ethylene is obtained if the drying agent MgSO4 . 2H(2)O is admired and the product 34 extracted. The gas/solid procedures avoid solvents and fuming nitric acid. They give pure products without necessity for recrystallization in most cases and they avoid wastes. Atomic force microscopy (AFM) measurements on prominent faces of single crystals of 1a, 11a, 28, and 33 reveal phase rebuildings with well-directed long-range molecular transports. Nanoliquids were only present on (110) of 28. The characteristic AFM features are correlated with known X-ray crystal structure data and compared with previous results. The shape of the features depends on the molecular packing in the crystal bulk and on the molecular shapes. Molecular interpretations of the AFM features are given.
• REACTION OF BENZYLAMINE WITH 3-NITROSO-2-OXAZOLIDONE¹
  作者：W. F. COCKBURN、A. F. McKAY

  DOI：10.1021/jo01131a015

  日期：1953.3
• The Reaction of Amines with 3-Nitroso-2-oxazolidone¹
  作者：A. F. McKay、E. J. Tarlton

  DOI：10.1021/ja01132a006

  日期：1952.6
• Gabriel, Chemische Berichte, 1905, vol. 38, p. 2394
  作者：Gabriel

  DOI：——

  日期：——
• SINGER, S. S., J. MED. CHEM., 1985, 28, N 8, 1088-1093
  作者：SINGER, S. S.

  DOI：——

  日期：——