4-methyl-5-phenyl-2,3-dihydro-1H-pyrazol-3-one | 7713-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-5-phenyl-2,3-dihydro-1H-pyrazol-3-one
• 英文别名: 4-methyl-5-phenyl-1,2-dihydro-3H-pyrazol-3-one；4-methyl-5-phenyl-1,2-dihydro-pyrazol-3-one；4-Methyl-5-phenyl-1,2-dihydro-pyrazol-3-on；NoName_698；4-methyl-5-phenyl-1,2-dihydropyrazol-3-one
• CAS: 7713-78-2
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: KITWZJXZJOOKTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-5-phenyl-2,3-dihydro-1H-pyrazol-3-one 在 氯 作用下， 生成 2-acetyl-4-chloro-4-methyl-5-phenyl-2,4-dihydro-pyrazol-3-one
  参考文献：
  名称：

  A New Synthesis of Unsaturated Acids. III. Structures of the Halogenation Products of 4-Unsubstituted and 4-Monosubstituted-2-pyrazolin-5-ones¹

  摘要：

  DOI：

  10.1021/ja01554a051
• 作为产物：
  描述：

  2-甲基-3-氧代-3-苯基丙酸乙酯 在 乙醇 、 一水合肼 作用下， 生成 4-methyl-5-phenyl-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  v. Auwers; Mauss, Journal fur praktische Chemie (Leipzig 1954), 1925, vol. <2> 110, p. 206

  摘要：

  DOI：

文献信息

• A simple approach to pyrazol-3-ones via diazenes
  作者：Bojan Burja、Marijan Kočevar、Slovenko Polanc

  DOI：10.1016/j.tet.2009.08.047

  日期：2009.10

  An efficient entry into pyrazol-3-ones is described starting from propenoic acids that were first transformed into the corresponding hydrazides. Oxidation of the hydrazides gave the diazenes and the latter cyclized to pyrazol-3-ones on treatment with ZrCl4. The methoxycarbonyl protection of the N-1 of the pyrazolone derivatives was easily removed under mild reaction conditions.

  描述了从首先被转化成相应的酰肼的丙烯酸开始有效地进入吡唑-3-酮。酰肼的氧化产生了二氮烯，并且在用ZrCl 4处理时将其环化成吡唑-3-酮。在温和的反应条件下，容易除去吡唑啉酮衍生物的N-1的甲氧基羰基保护基。
• 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。
• Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)
  作者：Rosimeire C. Barcelos、Lucas A. Zeoly、Manoel T. Rodrigues、Bruno R. V. Ferreira、Marcos N. Eberlin、Fernando Coelho

  DOI：10.1007/s00706-015-1427-6

  日期：2015.9

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.
• A New Synthesis of Unsaturated Acids. I. α,β-Acetylenic Acids^1,2
  作者：Louis A. Carpino

  DOI：10.1021/ja01536a021

  日期：1958.2
• DE934948
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