3-methyl-1-phenyl-5-(p-tolylthio)-1H-pyrazole-4-carbaldehyde | 308298-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-phenyl-5-(p-tolylthio)-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-methyl-5-[(4-methylphenyl)sulfanyl]-1-phenyl-1H-pyrazole-4-carbaldehyde；3-methyl-5-(4-methylphenyl)sulfanyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 308298-47-7
• 化学式: C₁₈H₁₆N₂OS
• 分子量: 308.404
• InChiKey: XPOFDIGSRPYDAG-UHFFFAOYSA-N

物化性质

• 沸点：
  459.6±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-1-phenyl-5-(p-tolylthio)-1H-pyrazole-4-carbaldehyde 在 叔丁基过氧化氢 、 1,3-dibutyl-1H-benzo[d]-[1,2,3]triazol-3-ium bromide 作用下， 以 水 为溶剂， 反应 24.0h， 以63%的产率得到3,6-dimethyl-1-phenylthiochromeno[2,3-c]pyrazol-4(1H)-one
  参考文献：
  名称：

  Green Method for the Synthesis of Chromeno[2,3-c]pyrazol-4(1H)-ones through Ionic Liquid Promoted Directed Annulation of 5-(Aryloxy)-1H-pyrazole-4-carbaldehydes in Aqueous Media

  摘要：

  The first classical heterocyclic ionic liquid (IL) promoted C-H bond oxidant cross-doupling,reaction for the intramolecular annulation of 5-(aryloxy)-1H-pyrazole-4-carbal- dehydes to chromeno[2,37c]pyrazol-4(1H)-ones has been disclosed The promoter 1,3-dibutyl-1H-benzo[d]fl 2 3]- triazol-34-ium bromide can be easily recycled reused with the same efficacies for at least five cycles in aqueous medium The strategy works smoothly and provides applicable protocol to construct a Wide range of products.

  DOI：

  10.1021/acs.orglett.5b00033
• 作为产物：
  描述：

  依达拉奉 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-methyl-1-phenyl-5-(p-tolylthio)-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Green Method for the Synthesis of Chromeno[2,3-c]pyrazol-4(1H)-ones through Ionic Liquid Promoted Directed Annulation of 5-(Aryloxy)-1H-pyrazole-4-carbaldehydes in Aqueous Media

  摘要：

  The first classical heterocyclic ionic liquid (IL) promoted C-H bond oxidant cross-doupling,reaction for the intramolecular annulation of 5-(aryloxy)-1H-pyrazole-4-carbal- dehydes to chromeno[2,37c]pyrazol-4(1H)-ones has been disclosed The promoter 1,3-dibutyl-1H-benzo[d]fl 2 3]- triazol-34-ium bromide can be easily recycled reused with the same efficacies for at least five cycles in aqueous medium The strategy works smoothly and provides applicable protocol to construct a Wide range of products.

  DOI：

  10.1021/acs.orglett.5b00033

文献信息

• One-Pot Multiсomponent Synthesis and Characterization of Some New Pyrazolylpyrazoline Scaffolds as Antitubercular and Antimalarial Agents
  作者：M. J. Zala、J. J. Vora

  DOI：10.1134/s1070428021100225

  日期：2021.10

  Abstract A new, facile, and environment friendly synthesis of some novel pyrazolylpyrazoline derivatives has been achieved using one-pot multicomponent reaction of substituted aromatic aldehydes, 2-acetylpyrrole or 2-acetyl-1,3-thiazole, and substituted hydrazines in the presence of sodium hydroxide in ethanol at room temperature under ultrasonication. The salient features of this green protocol are

  摘要 通过取代芳香醛、2-乙酰基吡咯或 2-乙酰基-1,3-噻唑和取代肼的一锅多组分反应，在乙醇中的氢氧化钠在室温下超声处理。这个绿色协议的显着特点是一锅反应、反应时间短和简单的后处理程序。所有合成的化合物都通过光谱技术进行了表征，并评估了它们的体外抗结核和抗疟活性。与标准药物相比，一些测试的化合物显示出良好的活性。
• Synthesis, characterization, in silico molecular docking study and biological evaluation of a 5-(phenylthio) pyrazole based polyhydroquinoline core moiety
  作者：Nirav H. Sapariya、Beena K. Vaghasiya、Rahul P. Thummar、Ronak D. Kamani、Kirit H. Patel、Parth Thakor、Sampark S. Thakkar、Arabinda Ray、Dipak K. Raval

  DOI：10.1039/c7nj01962a

  日期：——

  A multicomponent cyclocondensation reaction has been developed by incorporating 3-methyl-5-substituted phenylthio-1-phenyl-1H-pyrazole-4-carbaldehydes 3a–c, various enaminones 6a–c and different active methylene compounds 7a–c (malononitrile 7a/ethylcaynoacetate 7b/caynoacetamide 7c) in the presence of piperidine as a basic catalyst, to afford a combinatorial library of polyhydroquinoline scaffolds

  通过掺入3-甲基-5-取代的苯硫基-1-苯基-1 H-吡唑-4-甲醛3a–c，各种烯胺基6a–c和不同的活性亚甲基化合物7a–c（丙二腈7a），已开发出多组分环缩合反应。在哌啶为基础催化剂的情况下，将/乙基乙酰乙酸酯7b /乙酰乙酸乙酰胺7c）提供聚氢喹啉骨架的组合文库，即 8a–p。合成目标化合物的产率高至优异（71–84％）。所有合成的化合物均已通过1 H NMR表征，1313 C NMR，IR，质谱技术和元素分析。在体外评估所有合成的化合物的抗菌，抗结核和抗疟活性。一个在硅片分子对接研究，以及在硅片药代动力学评价已经进行了。这一新类别的许多候选人都表现出明显的针对一线药物的活动。
• Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group
  作者：Guiping Ouyang、Zhuo Chen、Xue-Jian Cai、Bao-An Song、Pinaki S. Bhadury、Song Yang、Lin-Hong Jin、Wei Xue、De-Yu Hu、Song Zeng

  DOI：10.1016/j.bmc.2008.09.070

  日期：2008.11

  Fourteen title compounds, 1-substituted-5-substitutedphenylthio-4-pyrazolaldoxime ester derivatives 4a-4n, were synthesized from the starting material 1-substitutedphenyl-3-methyl-5-substitutedphenylthio-4-pyrazolaldoximes 3 by treatment with acyl chloride. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were further confirmed by IR, 1H

  通过用酰氯处理，由起始原料1-取代苯基-3-甲基-5-取代苯硫基-4-吡唑醛肟3合成14个标题化合物，即1-取代-5-取代苯硫基-4-吡唑并肟肟酯衍生物4a-4n。通过物理常数表征合成的化合物，并通过IR，1 H NMR，13 C NMR和元素分析进一步证实标题化合物的结构。生物测定结果表明标题化合物具有弱到良好的抗TMV生物活性，其中4l具有对TMV CP的高亲和力，显着增强了烟叶的抗病性。
• Synthesis and Molecular Docking Study of Arylsulfanyl Pyrazolylpyrazoline Derivatives as Antitubercular Agents
  作者：M. J. Zala、J. J. Vora、V. M. Khedkar

  DOI：10.1134/s107042802112023x

  日期：2021.12
• Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety
  作者：Guiping Ouyang、Xue-Jian Cai、Zhuo Chen、Bao-An Song、Pinaki S. Bhadury、Song Yang、Lin-Hong Jin、Wei Xue、De-Yu Hu、Song Zeng

  DOI：10.1021/jf802489e

  日期：2008.11.12

  Target compounds 4a-n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaidoximes (3) with chloromethylated heterocyclic compounds (CICH2-R-3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a-e with KMnO4 in HOAc at room temperature afforded eight new compounds, 5a-h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, H-1 NMR, C-13 NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC50 = 58.7 and 65.3 mu g/mL) as the commercial product Ningnanmycin (EC50 = 52.7 mu g/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.