1-methylurazole | 34771-28-3

• 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-methylurazole
• 英文别名: 1-Methyl-1,2,4-triazolidine-3,5-dione
• CAS: 34771-28-3
• 化学式: C₃H₅N₃O₂
• 分子量: 115.092
• InChiKey: NENDRBATLNDSTO-UHFFFAOYSA-N

物化性质

• 熔点：
  241 °C
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯 、 1-methylurazole 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  铜催化脱芳香剂 1,2-氢氨化

  摘要：

  利用亲环体介导的光环加成和氢化铜催化，我们报道了非活化原料芳烃（包括苯和萘）的正式脱芳香加氢胺化。使用密度泛函理论 (DFT) 计算合理化了独特的选择性范式，并开发了可扩展的去对称化。这种转化能够有效地获得具有多个立体中心的密集功能化小分子。

  DOI：

  10.1002/anie.202407281
• 作为产物：
  描述：

  3-carbamoyl-3-methyl-carbazic acid ethyl ester 在 sodium hydroxide 作用下， 生成 1-methylurazole
  参考文献：
  名称：

  Arndt; Loewe; Tarlan-Akoen, Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya, 1948, vol. 13, p. 127

  摘要：

  DOI：
• 作为试剂：
  描述：

  苯酚 在 sodium tetrahydroborate 、 1-methylurazole 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (3S)-3-[4-[(2-氯-5-碘苯基)甲基]苯氧基]四氢呋喃
  参考文献：
  名称：

  一种恩格列净中间体的合成方法

  摘要：

  本发明公开了一种恩格列净关键中间体的合成方法。本发明采用由(S)‑3‑羟基四氢呋喃与苯酚在BINAP和MTAD作用下生成(S)‑3‑苯氧基四氢呋喃，然后与2‑氯‑5‑碘苯甲酸酰化反应得到2‑3(5‑碘‑2‑氯苯基)[4‑[[(3S)‑四氢‑3‑呋喃基]氧基]苯基]甲酮，最后还原得到(S)‑3‑(4‑(5‑碘‑2‑氯苄基)苯氧基)四氢呋喃。该方法与现有技术相比，反应步骤短，条件温和，后处理简单，产品的收率高。

  公开号：

  CN114213365A

文献信息

• Anti-cancer medicaments
  申请人：——

  公开号：US20040176395A1

  公开（公告）日：2004-09-09

  Novel compounds and methods of using those compounds for the treatment of oncological conditions are provided. In a preferred embodiment, modulation of the activation states of abl or bcr-abl &agr;-kinase proteins comprises the step of contacting the kinase proteins with the novel compounds.

  提供了用于治疗肿瘤病症的新化合物及使用这些化合物的方法。在一个优选实施例中，调节abl或bcr-abl&agr;-激酶蛋白的激活状态包括将激酶蛋白与新化合物接触的步骤。
• Dearomative Ring Expansion of Polycyclic Arenes
  作者：Paolo Piacentini、Tanner W. Bingham、David Sarlah

  DOI：10.1002/anie.202208014

  日期：2022.9.5

  A missing link between dearomative cyclopropanation and ring expansion of polycyclic (hetero)arenes has been established by utilizing an arenophile-based strategy. This two-step protocol enables the direct conversion of aromatic compounds into (aza)benzocycloheptatrienes, which are important structural motifs in natural products and biologically active compounds.

  通过利用基于亲烯体的策略，已经建立了脱芳环丙烷化和多环（杂）芳烃的扩环之间缺失的联系。这种两步协议可以将芳香族化合物直接转化为 (aza)benzocycloheptatrienes，这是天然产物和生物活性化合物中的重要结构基序。
• 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.
• Cuneo, Chemisches Zentralblatt, 1898, vol. 69, # I, p. 39
  作者：Cuneo

  DOI：——

  日期：——
• An Easy Access to Hydrazinocarbonyl Carbamic Acid Ethyl Esters
  作者：Gottfried Faleschini

  DOI：10.1007/pl00010213

  日期：1999.2