1-phenyl-4-methylurazole | 14500-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-4-methylurazole
• 英文别名: 4-methyl-1-phenyl-[1,2,4]triazolidine-3,5-dione；4-Methyl-1-phenyl-[1,2,4]triazolidin-3,5-dion；4-Methyl-1-phenyl-1,2,4-triazolidin-3,5-dion；1-Phenyl-4-methyl-urazol；4-Methyl-1-phenyl-urazol；1,2,4-Triazolidine-3,5-dione, 4-methyl-1-phenyl-；4-methyl-1-phenyl-1,2,4-triazolidine-3,5-dione
• CAS: 14500-23-3
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: XVVORNVNYKBZKT-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C
• 密度：
  1.327±0.06 g/cm3(Predicted)
• 溶解度：
  0.00 M

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-4-methylurazole 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 15.67h， 生成 3-Methyl-1-phenylspiro[1,3,5-triazinane-6,9'-fluorene]-2,4-dione
  参考文献：
  名称：

  Fluorenyl Participated Ring Transformation of Urazoles to Triazinanediones

  摘要：

  Fluorenylation of 1,4-disubstituted urazole (1) with 9-bromofluorene affords corresponding fluorenylurazole (2) along with the rearrangement product triazinanedione (3). The ratio of two products is closely related to the acidity of starting urazole (1). Compound (2) can be transformed into 3 upon treated with potassium t-butoxide. A mechanism involving N-acylimine as ring opening intermediate is proposed. The dual roles of urazole anion (1-K) are discussed.

  DOI：

  10.3987/com-00-9087
• 作为产物：
  描述：

  1-carbethoxy-2-phenyl-4-methylsemicarbazide 在 氢氧化钾 作用下， 反应 0.5h， 生成 1-phenyl-4-methylurazole
  参考文献：
  名称：

  Proton-transfer chemistry of urazoles and related imides, amides, and diacyl hydrazides

  摘要：

  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.

  DOI：

  10.1021/jo00019a034

文献信息

• A reinvestigation of the reactions between diazomethane and 1-phenylurazole
  作者：M. J. Bausch、L.-H. Wang

  DOI：10.1002/poc.610061102

  日期：1993.11

  separate experiments, the monomethylated species 5 and 6 were allowed to react with diazomethane in efforts to develop a sequence of reactions that reasonably accounts for the formation of 2–4. Whereas N- and O-methylated products were obtained when 5 was treated with ethereal diazomethane, the reaction of 6 and diazomethane produced only the N-alkylated product 1-phenyl–2,4-dimethylurazole (in quantitative

  使用醚重氮甲烷作为甲基化剂对1-苯基脲基（1）进行彻底的甲基化，形成三种产物：1-苯基-3,5-二甲氧基-1,2,4-三唑（2），1-苯基-3-甲氧基-4-甲基- Δ 2 -1,2,4- triazolinev5酮（3）和1-苯基-2,4- dimethylurazole（4）。基于分离的2-4的量，这些反应的总收率通常> 90％。当1和重氮甲烷被允许在导致一单甲基化的类似物的形成一种时尚，1-苯基-3-甲氧基- Δ反应2形成了1,2,4-三唑啉-5-酮（5）和1-苯基v2-甲基尿唑（6）。在单独的实验中，允许单甲基化的物种5和6与重氮甲烷反应，以努力开发合理解释2–4形成的一系列反应。而Ñ -和ö甲基化的5时用醚重氮甲烷处理，得到产品，6进行反应和重氮甲烷仅产生的Ñ-烷基化产物1-苯基–2,4-二甲基尿唑（定量收率）。这些实验的结果与一系列反应一致，在这些反应中，首先用重氮甲烷处理1，形
• N-haloalkylmio urazole pesticides
  申请人：——

  公开号：US04087534A1

  公开（公告）日：1978-05-02

  Novel haloalkylthio 4-substituted urazoles and thiourazoles of the formula: ##STR1## wherein R is alkyl of 1-12 carbon atoms, cycloalkyl having 3-6 carbon atoms, lower monohaloalkyl, benzyl, phenylethyl and phenyl optionally substituted by 1-3 halogens, nitro, chloromethyl, trifluoromethyl, lower alkyl, lower alkoxy or lower thioalkyl groups; R' designates haloalkyl of 1 or 2 carbon atoms, having at least two halogen atoms, and R" designates R or-SR', and X and Y each designate independently oxygen or sulfur: A process for preparing the above defined novel compounds, and fungistatic, fungicidal, bacteriostatic and bactericidal compositions of matter containing such compounds as active ingredient.

  新型卤代烷基硫代取代的4-尿唑啉和硫代尿唑啉的化学式为：##STR1## 其中，R表示1-12个碳原子的烷基，3-6个碳原子的环烷基，较低的单卤代烷基，苯甲基，苯基乙基和苯基，可选地被1-3个卤素，硝基，氯甲基，三氟甲基，较低烷基，较低烷氧基或较低硫代烷基基团取代；R'表示具有至少两个卤素原子的1或2个碳原子的卤代烷基，R"表示R或-SR'，X和Y各自独立地表示氧或硫：制备上述新型化合物的方法，以及包含该化合物作为活性成分的杀真菌，杀菌，抑菌和杀菌剂组成的物质。
• Acree, American Chemical Journal, 1907, vol. 38, p. 73,75
  作者：Acree

  DOI：——

  日期：——
• Acree, American Chemical Journal, 1902, vol. 27, p. 129
  作者：Acree

  DOI：——

  日期：——
• 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：——