2-(4-chlorophenyl)-4-[(4-chlorophenyl)(2-hydroxy-1-naphthyl)methyl]-5-methyl-2,3-dihydro-1H-pyrazol-3-one | 1334395-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-4-[(4-chlorophenyl)(2-hydroxy-1-naphthyl)methyl]-5-methyl-2,3-dihydro-1H-pyrazol-3-one
• 英文别名: 2-(4-Chlorophenyl)-4-[(4-chlorophenyl)-(2-hydroxy-1-naphthyl)methyl]-5-methyl-1H-pyrazol-3-one；2-(4-chlorophenyl)-4-[(4-chlorophenyl)-(2-hydroxynaphthalen-1-yl)methyl]-5-methyl-1H-pyrazol-3-one
• CAS: 1334395-27-5
• 化学式: C₂₇H₂₀Cl₂N₂O₂
• 分子量: 475.374
• InChiKey: HMWUSJJNUUAOLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  33
• 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：

  乙酰乙酸乙酯 、 4-氯苯甲醛 、 4-氯苯肼 、 2-萘酚 在 copper(I) iodide 作用下， 以 水 为溶剂， 反应 0.67h， 以91%的产率得到2-(4-chlorophenyl)-4-[(4-chlorophenyl)(2-hydroxy-1-naphthyl)methyl]-5-methyl-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication

  摘要：

  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.

  DOI：

  10.1016/j.ultsonch.2013.01.005

文献信息

• 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.