1-nitrohydantoin | 2825-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-nitrohydantoin
• 英文别名: 1-nitro-imidazolidine-2,4-dione；1-Nitro-imidazolidin-2,4-dion；Hydantoin, 1-nitro-；1-nitroimidazolidine-2,4-dione
• CAS: 2825-15-2
• 化学式: C₃H₃N₃O₄
• 分子量: 145.075
• InChiKey: JLADTIPBYWSGLM-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C (decomp)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-nitrohydantoin 、 alkaline earth salt of/the/ methylsulfuric acid 生成 亚硝酸
  参考文献：
  名称：

  Franchimont; van Erp, Recueil des Travaux Chimiques des Pays-Bas, 1896, vol. 15, p. 168

  摘要：

  DOI：
• 作为产物：
  描述：

  海因 在 nitronium trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69.2%的产率得到1-nitrohydantoin
  参考文献：
  名称：

  亲电四烷基硝酸铵硝化。一，方便的新型无水三氟甲磺酸硝鎓的合成和原位杂环氮的硝化

  摘要：

  硝酸四正丁基铵与三氟甲磺酸CF 3 SO 2 OSO 2 CF 3（Tf 2 O）在二氯甲烷（CH 2 Cl 2）溶剂中于0摄氏度下反应，生成无水硝酸硝氮，NO 2 OSO 2 CF 3（NO 2 OTf）。随后引入各种杂环及其N-乙酰化类似物，通过整体一锅法可得到20-76％的N-硝化产物。

  DOI：

  10.1016/s0040-4039(00)61671-4

文献信息

• Franchimont; Klobbie, Recueil des Travaux Chimiques des Pays-Bas, 1888, vol. 7, p. 14
  作者：Franchimont、Klobbie

  DOI：——

  日期：——
• Harries; Weiss, Justus Liebigs Annalen der Chemie, 1903, vol. 327, p. 383
  作者：Harries、Weiss

  DOI：——

  日期：——
• 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.
• Franchimont; Klobbie, Recueil des Travaux Chimiques des Pays-Bas, 1888, vol. 7, p. 238
  作者：Franchimont、Klobbie

  DOI：——

  日期：——
• Behrend; Osten, Justus Liebigs Annalen der Chemie, 1905, vol. 343, p. 154
  作者：Behrend、Osten

  DOI：——

  日期：——