4-[(2-hydroxy-1-naphthyl)(phenyl)methyl]-5-methyl-2-phenyl-2,3-dihydro-1H-3-pyrazolone | 1334395-16-2

• 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-[(2-hydroxy-1-naphthyl)(phenyl)methyl]-5-methyl-2-phenyl-2,3-dihydro-1H-3-pyrazolone
• 英文别名: 4-[(2-hydroxy-1-naphthyl)(phenyl)methyl]-5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one；4-[(2-Hydroxy-1-naphthyl)-phenyl-methyl]-5-methyl-2-phenyl-1H-pyrazol-3-one；4-[(2-hydroxynaphthalen-1-yl)-phenylmethyl]-5-methyl-2-phenyl-1H-pyrazol-3-one
• CAS: 1334395-16-2
• 化学式: C₂₇H₂₂N₂O₂
• 分子量: 406.484
• InChiKey: AIUKQQTVLYQBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯肼 在 Ni (II) complex with 1,2-di(4-pyridyl)ethylene immobilized on nano-silica gel 作用下， 以 neat (no solvent) 为溶剂， 反应 0.04h， 生成 4-[(2-hydroxy-1-naphthyl)(phenyl)methyl]-5-methyl-2-phenyl-2,3-dihydro-1H-3-pyrazolone
  参考文献：
  名称：

  Nano-SiO2@nPr@DPyE-Ni：一种用于快速生产对称二芳基硫醚和吡唑啉酮的新型纳米催化剂

  摘要：

  最初，制备了一种以纳米硅胶为基质、Ni活性中心的新型有机金属催化剂，即纳米SiO 2 @nPr@DPyE-Ni，并对其性能进行了深入的争论。然后以优异的性能应用于生产对称二芳基硫醚（14 个条目，78–98%，20–150 分钟，EtOH，70 °C）和 2-芳基-5-甲基-2,3-二氢-1 H -3-吡唑啉酮（12 个条目，91–98%，2–4 分钟，无溶剂，室温）。在两条生产路线中，纳米催化剂均可回收和重复使用七次以上，并通过回收结果、热过滤测试和ICP-OES（耦合等离子体发射光谱）方法检查和确认其异质性。 图形概要

  DOI：

  10.1007/s11164-024-05296-4

文献信息

• Ce/SiO2 composite as an efficient catalyst for the multicomponent one-pot synthesis of substituted pyrazolones in aqueous media and their antimicrobial activities
  作者：Adinarayana Murthy Akondi、Mannepalli Lakshmi Kantam、Rajiv Trivedi、Jagadeesh Bharatam、Sahitha Phani Babu Vemulapalli、Suresh K. Bhargava、Sudheer Kumar Buddana、Reddy Shetty Prakasham

  DOI：10.1016/j.molcata.2015.11.004

  日期：2016.1

  We describe here the preparation and characterization of a Ce/SiO2 catalyst and its application in an eco-friendly and convenient synthesis of pyrazolone derivatives via one-pot multicomponent reaction of 2-naphthol, aldehydes, phenylhydrazine and ethyl acetoacetate under aqueous media. The catalyst was prepared using sol-gel method and characterized by XRD, XPS, UV-DRS, SEM, TEM and surface area analysis

  我们在这里描述了Ce / SiO 2催化剂的制备和表征，及其在水介质下通过2-萘酚，醛，苯肼和乙酰乙酸乙酯的一锅多组分反应在吡喃酮衍生物的生态友好和方便的合成中的应用。该催化剂采用溶胶-凝胶法制备，并通过XRD，XPS，UV-DRS，SEM，TEM和表面积分析对其进行表征。利用2D NMR技术确定吡唑啉酮互变异构体。对新化合物的抗微生物活性进行了评估，并对大多数测试的细菌和真菌菌株表现出良好至有希望的活性。
• Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication
  作者：Abolfazl Ziarati、Javad Safaei-Ghomi、Sahar Rohani

  DOI：10.1016/j.ultsonch.2013.01.005

  日期：2013.7

  A simple and green process to prepare copper iodide in nano scale via sonication was carried out. Subsequently, this nanoparticles was used as an efficient catalyst for the synthesis of 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones via four-component reaction of hydrazine, ethyl acetoacetate, aldehyde and beta-naphthol in water under ultrasound irradiation. The combinatorial synthesis was attained for this procedure with applying ultrasound irradiation while making use of water as green ambient. Simple work-up, excellent yield of products and short reaction times are some of the important features of this protocol. Notably, this catalyst could be recycled and reused for five times without noticeably decreasing the catalytic activity. (C) 2013 Elsevier B.V. All rights reserved.
• A facile four-component sequential protocol in the expedient synthesis of novel 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones in water and their antitubercular evaluation
  作者：Pethaiah Gunasekaran、Subbu Perumal、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2011.07.029

  日期：2011.9

  A series of 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones has been synthesized by one-pot, four-component sequential reactions of phenylhydrazine, methyl acetoacetate, aromatic aldehydes and beta-naphthol in the presence of p-toluenesulphonic acid in water in good yields. These 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones were screened for in-vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among the 15 compounds screened, 4-[(2,4-dichlorophenyl)(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-2,3-dihydro-1H-3-pyrazolone displays the maximum potency with a minimum inhibitory concentration (MIC) of 1.6 mu M against MTB, being 2.94 and 4.75 times more active than ciprofloxacin and ethambutol respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.