1-Methyl-4-phenyl-1,2,4-triazolidin-3,5-dion | 28538-67-2

• 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-Methyl-4-phenyl-1,2,4-triazolidin-3,5-dion
• 英文别名: 1-methyl-4-phenylurazole；Methyl-phenylurazol；1-methyl-4-phenyl-[1,2,4]triazolidine-3,5-dione；1-Methyl-4-phenyl-[1,2,4]triazolidin-3,5-dion；1-Methyl-4-phenylurazol；1-Phenyl-3-methylurazol；1-Methyl-4-phenyl-1,2,4-triazolidine-3,5-dione
• CAS: 28538-67-2
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: RJNRHWZMHWQLBU-UHFFFAOYSA-N

物化性质

• 密度：
  1.327±0.06 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-Methyl-4-phenyl-1,2,4-triazolidin-3,5-dion 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 15.67h， 生成 1-Methyl-3-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-Ethoxycarbonyl-2-methyl-4-phenylsemicarbazid 在 氢氧化钾 作用下， 生成 1-Methyl-4-phenyl-1,2,4-triazolidin-3,5-dion
  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
• 作为试剂：
  描述：

  DRVAIHPF 在 rose bengal 、 1-Methyl-4-phenyl-1,2,4-triazolidin-3,5-dion 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 C₄₄H₆₅N₁₃O₁₂
  参考文献：
  名称：

  Proximity Histidine Labeling by Umpolung Strategy Using Singlet Oxygen

  摘要：

  DOI：

  10.1021/jacs.1c01626

文献信息

• 1-Methyl-4-aryl-urazole (MAUra) labels tyrosine in proximity to ruthenium photocatalysts
  作者：Shinichi Sato、Kensuke Hatano、Michihiko Tsushima、Hiroyuki Nakamura

  DOI：10.1039/c8cc02891e

  日期：——

  as substrates to evaluate the photocatalyst-proximity dependences of candidates for tyrosine labelling reagents. The 1-methyl-4-aryl-urazole (MAUra) structure was found to be a novel tyrosyl radical trapping agent to label tyrosine residues effectively under the conditions where the ruthenium photocatalyst and tyrosine were in close proximity. Using a ruthenium photocatalyst conjugated to a carbonic

  我们设计并合成了与脯氨酸接头和钌光催化剂偶联的肽。这些肽用作底物，以评估酪氨酸标记试剂候选物对光催化剂的依赖性。发现1-甲基-4-芳基-脲基（MAUra）结构是一种新型的酪氨酰基自由基捕获剂，可在钌光催化剂和酪氨酸非常接近的条件下有效地标记酪氨酸残基。使用与碳酸酐酶配体偶联的钌光催化剂，通过叠氮化物或脱硫生物素偶联的MAUra衍生物以显着的靶标选择性标记复合蛋白混合物中的靶蛋白。
• Umsetzung von amino-aziminen mit basen
  作者：Egon Fahr、Monika J. Richter、Wolfgang Schmitt-Sody、Rainer Elbert

  DOI：10.1016/s0040-4039(00)78664-3

  日期：1980.1

  Amino-azimines of type (1) react at room temperature with bases (ammonia, aliphatic amines, hydrazine and methyl-hydrazine, aqueous/ethanolic sodium hydroxide) by cleavage of the to the and the NNN moieties (azide).

  （1）型的氨基叠氮化物在室温下通过裂解NH3和N3N3N4部分（叠氮化物）与碱（氨，脂肪族胺，肼和甲基肼，含水/乙醇氢氧化钠）反应。 。
• BICYCLIC COMPOUNDS AS PESTICIDES
  申请人：Bayer CropScience Aktiengesellschaft

  公开号：US20190297887A1

  公开（公告）日：2019-10-03

  The present application relates to novel bicyclic compounds, to compositions comprising these compounds, to the use thereof for control of animal pests and to processes and intermediates for the preparation thereof.

  本申请涉及新颖的双环化合物，包括这些化合物的组合物，其用于控制动物害虫的使用以及制备这些化合物的过程和中间体。
• Carbimid- und Carbonyl-Cyclisierungen von Semicarbaziden
  作者：Gerwalt Zinner、Michael Heitmann

  DOI：10.1002/ardp.19813140302

  日期：——

  Substituierte Semicarbazide werden mit Carbimiddichloriden und Phosgen zu fünfgliedrigen Heterocyclen acyliert; es entstehen Derivate des 1,3,4‐Oxadiazol‐ bzw. des 1,2,4‐Triazol‐Systems.

  Substituierte Semicarbazide werden mit Carbimiddichloride und Phosgen zu fünfgliedrigen Heterocyclen acyliert; es entstehen Derivate des 1,3,4-Oxadiazol-bzw。des 1,2,4-三唑系统。
• 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。