1,2,4-trimethyl-1,2,4-triazolidine-3,5-dione | 34874-04-9

• 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: 1,2,4-trimethyl-1,2,4-triazolidine-3,5-dione
• 英文别名: 1,2,4-trimethylurazole；1,2,4-Trimethylurazol；Trimethyl-[1,2,4]triazolidin-3,5-dion
• CAS: 34874-04-9
• 化学式: C₅H₉N₃O₂
• 分子量: 143.145
• InChiKey: RHUJUWUOLJJHCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C(Solv: ligroine (8032-32-4))
• 沸点：
  161.5±23.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  尿唑 、 硫酸二甲酯 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 12.0h， 以86.2%的产率得到1,2,4-trimethyl-1,2,4-triazolidine-3,5-dione
  参考文献：
  名称：

  Racemic 1,2,4-Trimethylurazole

  摘要：

  The structural and stereochemical parameters of 1,2,4-trimethyl-1,2,4-triazolidine-3,5-dione, C5H9N3O2, (1), were examined in view of the contrast between its physical properties and those of urazoles having one or more unsubstituted NW groups. The X-ray structure shows that (1) is devoid of intermolecular hydrogen bonding but retains the structural features of strongly hydrogen-bonded urazoles. Its trans-H(3)e-N-CH3 torsion angle of 72.3(5)degrees is trans-H3C-N-N-CH3 than the corresponding angle in urazoles having an unsubstituted or monamethylated N-N function, but smaller than that in urazoles monosubstituted with bulkier groups. Like other crystalline urazoles, (1) is racemic by virtue of N1 and N2 chirality. In its packing pattern of parallel molecular sheets, two pass through the unit cell; within a sheet, each molecule is surrounded by two of its own chirality and four of opposite chirality. While physical properties of crystalline urazoles can be associated with their degree of intermolecular hydrogen bonding, this study shows that their chirality is an intrinsic molecular phenomena.

  DOI：

  10.1107/s0108270196011894

文献信息

• Proton-transfer chemistry of urazoles and related imides, amides, and diacyl hydrazides
  作者：M. J. Bausch、B. David、P. Dobrowolski、C. Guadalupe-Fasano、R. Gostowski、D. Selmarten、V. Prasad、A. Vaughn、L. H. Wang

  DOI：10.1021/jo00019a034

  日期：1991.9

  Equilibrium acidity constants have been determined for 1,2,4-triazolidine-3,5-dione (urazole), several substituted urazoles, and other related acids, in both dimethyl sulfoxide (DMSO) and aqueous solution. In DMSO, urazole has a pK(a) of 13.1. In water, urazole has a pK(a) of 5.8. In general, N-methyl and N-phenyl substituents are found to acidify the urazole moiety, in both DMSO and water. The acidifying effects of these substituents are attenuated by a factor of 3.3 in water. The solvent effects are ascribed to the aqueous stabilization of urazole anions via hydrogen-bonding interactions and the aqueous-promoted relief of lone pair-lone pair electronic interactions that manifest themselves upon deprotonation of a hydrazyl proton in 1 and related species. That a hydrazyl proton in 1 is at least as acidic as the imide proton in 1 is comparison of C-13 NMR spectra for the urazoles and related nitrogen acids with C-13 spectra for the conjugate bases derived from these species. Upon loss of an imide proton, in both DMSO-d6 and D2O solutions, carbonyl carbon atoms present in succinimide as well as appropriately substituted urazoles and hydantoins experience substantial (13-17 ppm) downfield shifts. In contrast, deprotonation of 4-substituted and 1,4-substituted urazoles, 4,4-dimethylpyrazolidine-3,5-dione, and diacetylhydrazine (species that contain hydrazyl acidic protons) results in shifts in the positions of the carbonyl resonances that range from 5 ppm upfield to 3 ppm downfield. Deprotonation of species containing both imide and hydrazyl protons (i.e., urazole and 1-substituted urazoles) results in shifts in the carbonyl carbon resonances consistent with hydrazyl proton removal. Comparison of DMSO-phase pK(a)'s for acetamide (25.5), diacetylhydrazine (16.7), 4,4-dimethylpyrazolidine-3,5-dione (13.5), and urazole (13.5), and urazole (13.1) suggest that the remarkable acidity of the hydrazyl proton in urazole and substituted urazoles is due mainly to its cyclic diacyl hydrazide structure.
• Arndt; Loewe; Tarlan-Akoen, Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya, 1948, vol. 13, p. 127
  作者：Arndt、Loewe、Tarlan-Akoen

  DOI：——

  日期：——
• Racemic 1,2,4-Trimethylurazole
  作者：C. Y. Meyers、H. G. Lutfi、Y. Hou、P. D. Robinson

  DOI：10.1107/s0108270196011894

  日期：1997.1.15

  The structural and stereochemical parameters of 1,2,4-trimethyl-1,2,4-triazolidine-3,5-dione, C5H9N3O2, (1), were examined in view of the contrast between its physical properties and those of urazoles having one or more unsubstituted NW groups. The X-ray structure shows that (1) is devoid of intermolecular hydrogen bonding but retains the structural features of strongly hydrogen-bonded urazoles. Its trans-H(3)e-N-CH3 torsion angle of 72.3(5)degrees is trans-H3C-N-N-CH3 than the corresponding angle in urazoles having an unsubstituted or monamethylated N-N function, but smaller than that in urazoles monosubstituted with bulkier groups. Like other crystalline urazoles, (1) is racemic by virtue of N1 and N2 chirality. In its packing pattern of parallel molecular sheets, two pass through the unit cell; within a sheet, each molecule is surrounded by two of its own chirality and four of opposite chirality. While physical properties of crystalline urazoles can be associated with their degree of intermolecular hydrogen bonding, this study shows that their chirality is an intrinsic molecular phenomena.