3-Phenyl-1-(o-tolyl)-pyrazolon-(5) | 87277-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Phenyl-1-(o-tolyl)-pyrazolon-(5)
• 英文别名: 2-(2-methylphenyl)-5-phenyl-4H-pyrazol-3-one
• CAS: 87277-67-6
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: UERBMJDVOUAVMX-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C
• 沸点：
  381.1±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Phenyl-1-(o-tolyl)-pyrazolon-(5) 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium tert-butylate 、 氢气 、 三溴化磷 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 3-phenyl-1-p-tolyl-1H-pyrazole
  参考文献：
  名称：

  Palladium-catalyzed dehalogenation of 5-halopyrazoles

  摘要：

  AbstractA new and efficient method for the dehalogenation of 5‐halopyrazoles was developed by using the catalytic amount of palladium (II) chloride and triphenylphosphine as a ligand at reflux under constant flow of hydrogen gas. The reaction gave the corresponding pyrazole products in good to excellent yields (≥83%). J. Heterocyclic Chem., (2012).

  DOI：

  10.1002/jhet.845
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 (2-甲基苯基)肼 在 溶剂黄146 作用下， 生成 3-Phenyl-1-(o-tolyl)-pyrazolon-(5)
  参考文献：
  名称：

  吡咯烷酮与铜-亚烯基的不对称[3 + 3]环状：手性1,4-二氢吡喃并[2,3- c ]吡唑的合成

  摘要：

  乙炔基苯并恶嗪酮与吡唑啉酮的铜催化不对称环化[3 + 3]已实现，可轻松获得1,4-二氢吡喃并[2,3- c ]吡唑衍生物，且产率中等至优异，对映选择性极佳（高达99 ％ee）。与以前的乙炔基苯并恶嗪酮的铜-亚烯基环化反应相比，当前反应将炔丙基部分的三个碳原子融合成杂环骨架。

  DOI：

  10.1021/acs.orglett.8b02214

文献信息

• Synthesis of 4‐Alkenylated Pyrazolinones by 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)‐Mediated Oxidative Coupling Reaction
  作者：Yuhui Tao、Huafang Gu、Hongshuang Xia、Hongjiao Yang、Jinghua Li、Xiaoliang Xu、Dongping Cheng

  DOI：10.1002/ejoc.202201480

  日期：2023.2.13

  Synthesis of 4-alkenylated pyrazolinones derivatives by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of 1,3-diarylpropenes with pyrazolinones. The methodology has the advantages of metal-free, one-pot, high atom economy, and mild condition.

  通过 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 介导的 1,3-二芳基丙烯与吡唑啉酮的氧化偶联反应合成 4-烯基化吡唑啉酮衍生物。该方法具有无金属、一锅法、原子经济性高、条件温和等优点。
• A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH₃OK
  作者：Jingxiong Lai、You Huang

  DOI：10.1039/d3cc05751h

  日期：——

  A CH₃OK catalyzed [5+1] annulation was developed using a newly designed allene with 1,5-biselectroephilic properties.

  利用一种新设计的具有 1,5 双嗜酸特性的烯烃，开发了一种 CH3OK 催化的 [5+1] 环化反应。
• New investigation of Vilsmeier-type reaction using pyrazolones with various amides
  作者：Yu-Ying Huang、Kimiyoshi Kaneko、Hiroyuki Takayama、Masayuki Kimura、Fung Fuh Wong

  DOI：10.1016/j.tetlet.2011.05.055

  日期：2011.7

  New investigation of Vilsmeier-type reaction was evaluated to realize the solvent effect by using pyrazolones to react with various of amides, including formamide, N-methylformamide, N-propylformamide, N-tert-butylformamide, N,N-dimethylformamide (DMF), N,N-diethylformamide (DEF), N,N-dipropylformamide (DPF), N,N-diisopropylformamide, N,N-dibutylformamide, piperidine-l-carbaldehyde, and pyrrolidine-l-carbaldehyde, in the presence of phosphorous oxychloride POCl3. The unexpected resulting products were observed in this work according to the difference chemoseletivities of substituted amides. The plausible reactive pathways were proposed to explain the experimental result. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• A New and Convenient Method for the Synthesis of 1,3-Disubstituted 4,6,6-Trimethyl-1, 6-dihydropyrano[2,3-<i>c</i>]pyrazoles
  作者：Seiichi Matsugo、Mitsuo Saito、Akira Takamizawa

  DOI：10.1055/s-1983-30393

  日期：——
• Novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethane derivatives using formamide or N-methylformamide
  作者：Fung Fuh Wong、Yu-Ying Huang

  DOI：10.1016/j.tet.2011.03.089

  日期：2011.5

  A novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethanes was developed by reacting pyrazolones with formamide or N-methylformamide in the presence of phosphorous oxychloride POCl3 coupling agent. This method can efficiently provide a series of dipyrazolylmethane derivatives as the main products in excellent yields without the formylated products. Our experimental result was different with the classical Vilsmeier-type reaction. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.