meso-3,3',4,4'-tetramethyl-1,1'-diphenyl-[4,4'-bipyrazol]-5,5'-dione | 2969-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: meso-3,3',4,4'-tetramethyl-1,1'-diphenyl-[4,4'-bipyrazol]-5,5'-dione
• 英文别名: meso-3,3′,4,4′-tetramethyl-1,1′-diphenyl-[4,4′-bipyrazol]-5,5′-dione；meso-4,5,4',5'-tetramethyl-2,2'-diphenyl-2,4,2',4'-tetrahydro-[4,4']bipyrazolyl-3,3'-dione；meso-4,5,4',5'-Tetramethyl-2,2'-diphenyl-2,4,2',4'-tetrahydro-[4,4']bipyrazolyl-3,3'-dion；(4R)-4-[(4S)-3,4-dimethyl-5-oxo-1-phenylpyrazol-4-yl]-4,5-dimethyl-2-phenylpyrazol-3-one
• CAS: 2969-29-1
• 化学式: C₂₂H₂₂N₄O₂
• 分子量: 374.442
• InChiKey: RTKZPUFORVKLBP-SZPZYZBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基-3,4-二甲基异唑 、 苯肼 生成 meso-3,3',4,4'-tetramethyl-1,1'-diphenyl-[4,4'-bipyrazol]-5,5'-dione
  参考文献：
  名称：

  Kano, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 383,386

  摘要：

  DOI：

文献信息

• Mild Nitration of Pyrazolin‐5‐ones by a Combination of Fe(NO ₃ ) ₃ and NaNO ₂ : Discovery of a New Readily Available Class of Fungicides, 4‐Nitropyrazolin‐5‐ones
  作者：Igor B. Krylov、Alexander S. Budnikov、Elena R. Lopat'eva、Gennady I. Nikishin、Alexander O. Terent'ev

  DOI：10.1002/chem.201806172

  日期：2019.4.23

  4‐Nitropyrazolin‐5‐ones have been synthesized by the nitration of pyrazolin‐5‐ones at room temperature by employing the Fe(NO3)3/NaNO2 system. The method demonstrated selectivity towards the 4‐position of pyrazolin‐5‐ones even in the presence of NPh and allyl substituents, which are sensitive to nitration. It was shown that other systems containing FeIII and nitrites, namely Fe(NO3)3/tBuONO, Fe(ClO4)3/NaNO2

  通过使用Fe（NO 3）3 / NaNO 2体系在室温下硝化吡唑啉-5-酮合成了4-硝基吡唑啉-5-酮。即使存在对硝化敏感的NPh和烯丙基取代基，该方法也显示出对吡唑啉-5-酮的4位选择性。结果表明，其他含有Fe III和亚硝酸盐的体系，即Fe（NO 3）3 / t BuONO，Fe（ClO 4）3 / NaNO 2和Fe（ClO 4）3 / t BuONO，也是有效的。大概是铁三氧化亚硝酸盐（NaNO 2或t BuONO）形成NO 2自由基，作为吡唑啉-5-酮的硝化剂。已发现合成的4-硝基吡唑啉-5-酮是一类新的杀菌剂。发现它们对植物致病真菌的体外活性与商业杀真菌剂（氟康唑，克霉唑，三唑酮和克雷索肟）相当甚至更好。这些结果为开发新型植物保护剂提供了一个有希望的起点，这种保护剂可以很容易地从广泛使用的试剂中合成。
• Huettel,R.; Authaler,A., Chemische Berichte, 1963, vol. 96, p. 2879 - 2893
  作者：Huettel,R.、Authaler,A.

  DOI：——

  日期：——
• Veibel, Acta Chemica Scandinavica (1947), 1972, vol. 26, p. 3685,3689
  作者：Veibel

  DOI：——

  日期：——
• Radikalreaktionen an N-Heterocyclen. XI [1] Reaktionen von 3-Methyl-pyrazolin-5-onen mit Phenoxyl-Radikalen
  作者：Manfred Schulz、Michael Meske

  DOI：10.1002/prac.19933350706

  日期：——

  Pyrazolin-5-ones (3a-4) were oxidized with 2,4,6-trisubstituted phenoxy radicals (2a-d) to the corresponding radicals (4a-i), which dimerised or combined with phenoxy radical (2a) depending on the R1- and R4-substituents in (3). In the case of 3-methyl-1-phenyl-pyrazolin-5-one (3f) the primary radical combination products were not found, but the corresponding quinone methide (17) and the o-phenol derivative (18) were isolated. Products and yields have been investigated as a function of mol ratio substrate: oxidant and solvent. The radical combination products (7-10) could de-tertbutylated in the presence of aluminium chloride or in the presence of trifluoroarcetic acid, forming heterocyclic substituted phenols (21) and (22).
• Veibel; Westoeoe, Acta Chemica Scandinavica (1947), 1953, vol. 7, p. 119,123, 125
  作者：Veibel、Westoeoe

  DOI：——

  日期：——