4-(2-chloroacetyl)-5-methyl-2-phenyl-1H-pyrazol-3-one | 37703-60-9

• 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-chloroacetyl)-5-methyl-2-phenyl-1H-pyrazol-3-one
• 英文别名: 2-chloro-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethan-1-one；2-chloro-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone；1-phenyl-3-methyl-4-chloroacetyl-5-pyrazolone；4-chloroacetyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one
• CAS: 37703-60-9
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: KGIGCXKJNIFWPF-UHFFFAOYSA-N

物化性质

• 沸点：
  399.4±37.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(2-chloroacetyl)-5-methyl-2-phenyl-1H-pyrazol-3-one 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到3-methyl-1-phenyl-1H-furo[2,3-c]pyrazol-4-(5H)-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives

  摘要：

  In continuation of our efforts to find a new class of antimicrobial agents, a series of 4-hetarylpyrazoles and furo[2,3-c]pyrazoles were prepared via the reaction of 2-chloro-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone ( 1) with an appropriate nucleophilic reagents. These compounds were screened for their antibacterial activity against Gram-positive bacteria (Bacillus subtilis and Bacillus thuringiensis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) and antifungal activity against Fusarium oxysporum and Botrytis fabae. Among the synthesized compounds, 1-(5-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-yl)-2-methylfuran-3-yl)ethanone (12) showed equal activity with chloramphenicol against B. subtilis (MIC 3.125 mu g/mL), while its activity was 50% lower than of chloramphenicol against B. thuringiensis. N-[(4Z)-3-Methyl-1-phenyl-1H-furo[2,3-c]pyrazol-4(5H)-ylidene]-1H-benzimidazol-2-amine (7) and 2-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-4H-furo [3,2-c]chromen-4-one (13) were found to exhibit the most potent in vitro antifungal activity with MICs (6.25 mu g/mL) against B. fabae and F. oxysporum. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.045
• 作为产物：
  描述：

  氯乙酰氯 、 3-甲基-1-苯基-1H-吡唑-5-醇 在 calcium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-(2-chloroacetyl)-5-methyl-2-phenyl-1H-pyrazol-3-one
  参考文献：
  名称：

  离子液体萃取系统上带有β-二酮片段的二氮杂皇冠醚的协同分子内相互作用

  摘要：

  新型萃取剂β-二酮取代的diaza-18-crown-6表现出非常高的效率 萃取分子内协同作用对Sr 2+的影响离子液体萃取系统和从水中回收Sr 2+。离子液体 在酸性条件下成功实现。

  DOI：

  10.1039/b904596c

文献信息

• Synthesis and NMR-Spectroscopic Investigations with 4-Chloroacyl-1-phenylpyrazolin-5-ones
  作者：Gernot A. Eller、Wolfgang Holzer

  DOI：10.1002/jhet.3015

  日期：2018.1

  The synthesis of various 4‐acylpyrazolones bearing in the acyl moiety either a terminal chloro‐substituent or a terminal ortho‐chlorophenyl group was achieved by reaction of 3‐methyl‐1‐phenyl‐2‐pyrazolin‐5‐one (tautomer to 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol) with the corresponding acid chloride using calcium hydroxide / 1,4‐dioxane. In one case (reaction with chlorobutanoyl chloride) a spontaneous cyclization

  通过3-甲基-1-苯基-2-吡唑啉-5-互变异构体（互变异构体为3-甲基-1-苯基-1 H-吡唑-5-醇）与相应的酰氯一起使用氢氧化钙/ 1,4-二恶烷。在一种情况下（与氯丁酰氯反应），发生了自发环化反应，从而导致了相应的氧代庚并[2,3- c ]吡唑。对所有制备的化合物进行了详细的NMR光谱研究。
• Transformations of naproxen into pyrazolecarboxamides: search for potent anti-inflammatory, analgesic and ulcerogenic agents
  作者：Abdullah G. El-Sehemi、Samir Bondock、Yousry A. Ammar

  DOI：10.1007/s00044-013-0650-0

  日期：2014.2

  derivatives of naproxen were synthesized through the reaction of naprexenoyl chloride with amine derivatives containing pyrazole moiety. The synthesized compounds were screened for anti-inflammatory, analgesic, and ulcerogenic activities. Screening of anti-inflammatory revealed that compound 5 having a 1,3-diphenyl-pyrazol-4-yl moiety had the most promising activity. Compounds 8, 9, and 12, possessing 3

  萘普生酰肼与甲酰基吡唑，乙酰丙酮，烯胺酮，曼尼希碱和芳基肼基苯甲腈衍生物反应合成了许多含有各种吡唑甲酰胺的萘普生衍生物。同样，萘普生的许多衍生物是通过萘普烯二酰氯与含有吡唑部分的胺衍生物反应而合成的。筛选合成的化合物的抗炎，止痛和促溃疡活性。抗炎剂的筛选显示具有1，3-二苯基-吡唑-4-基部分的化合物5具有最有希望的活性。化合物8，9，和12分别具有3,5-二甲基-吡唑-1-基，3-苯基-吡唑-1-基和3,5-二氨基-4-（4-甲氧基苯基偶氮）-吡唑-1-基的，显示中等活动。而且，化合物8和12显示出比参考药物更高的镇痛活性。具有致溃疡作用的是具有甲氧苯基吡唑啉部分的化合物22，没有致溃疡作用。
• A simple synthesis of novel extraction reagents. 4-Acyl-5-pyrazolone-substituted crown ethers
  作者：Shoko Yamazaki、Miho Hanada、Yuichiro Yanase、Chizue Fukumori、Kaoru Ogura、Takashi Saeki、Shigeo Umetani

  DOI：10.1039/a809589b

  日期：——

  A synthesis of novel 4-acylpyrazol-5-one-substituted crown ethers metal-chelating reagents is described. 4-Acylpyrazol-5-one-substituted dibenzo-16-crown-5 1a, 4-acylpyrazol-5-one-substituted dibenzo-19-crown-6 1b, and bis(4-acylpyrazol-5-one)-substituted diaza-18-crown-6 1c were designed and synthesized by simple coupling reactions between α-chloro 4-acylpyrazol-5-one 3 and the corresponding crown ethers 2a–c. Compound 1a was found to be an effective and metal ion-selective extraction reagent.

  本文描述了新型4-酰基吡唑-5-酮取代的冠醚金属螯合试剂的合成。通过α-氯4-酰基吡唑-5-酮3与相应的冠醚2a-c之间的简单偶联反应，设计并合成了4-酰基吡唑-5-酮取代的二苯并-16-冠醚-5 1a、4-酰基吡唑-5-酮取代的二苯并-19-冠醚-6 1b和双(4-酰基吡唑-5-酮)取代的二氮杂-18-冠醚-6 1c。化合物1a是一种有效且具有金属离子选择性的萃取试剂。
• Self-assembly of arene ruthenium acylpyrazolone fragments to tetranuclear metallacycles. Molecular structures and solid-state ¹⁵N CPMAS NMR correlations
  作者：Riccardo Pettinari、Fabio Marchetti、Claudio Pettinari、Francesca Condello、Brian W. Skelton、Allan H. White、Michele R. Chierotti、Roberto Gobetto

  DOI：10.1039/c6dt00168h

  日期：——

  spectroscopic methods and the solid-state structures of mononuclear and tetranuclear complexes have been determined by single-crystal X-ray diffraction. The hapticity of the acylpyrazolone ligands to the Ru metal centre has also been established by 13C and 15N CPMAS NMR spectroscopy for the complexes where the lack of crystallinity prevented the elucidation of the crystal structure by SCXRD data.

  的[（η反应6 -cymene）的Ru（μ-Cl）的CL] 2与配体acylpyrazolone HQ“（HQ'一般;详细地说，HQ CH 2氯= 2-氯-1-（5-羟基-3-甲基-1-苯基-1 H-吡唑-4-基）乙酮），HQ hex = 1-（5-羟基-3-甲基-1-苯基-1 H-吡唑-4-基）庚烷-1-酮），HQ nPe = 1-（5-羟基-3-甲基-1-苯基-1 H-吡唑-4-基）-3,3-二甲基丁烷-1-酮）），在碱的存在下，得到相应的[（η 6 -cymene）的Ru（Q'）CL]单核络合物。它们与AgX反应（其中X = O 3 SCF 3或BF 4）在无水丙酮，得到阳离子metalla周期[（η 6 -cymene）的Ru（Q'）] 4（X）4。通过分析和光谱学方法对配合物进行了充分表征，并通过单晶X射线衍射确定了单核和四核配合物的固态结构。还通过13 C和15 N CPMAS
• Synthesis and crystal structure of 2-anilino-6H-5-(1-phenyl-3-methyl-5-pyrazolone-4-ylene)-1,3,4-thiadiazine
  作者：Guang-Fei Liu、Lang Liu、Dian-Zeng Jia、Kai-Bei Yu

  DOI：10.1007/s10870-004-7716-2

  日期：2004.12

  A novel pyrazolone derivative 2-anilino-6H-5-(1-phenyl-3-methyl-5-pyrazolone-4-ylene)-1,3,4-thiadiazine (PMCP-PTSC) containing NNS hexa-atomic heterocycle has been obtained and characterized by means of single crystal X-ray diffraction, IR and 1H NMR spectroscopies. It is interesting that when grown from two different solvents, two different crystalline structures are formed. The monoclinic crystal A belongs to a P21/c space group. The unit cell parameters are a = 16.414(4) Å, b = 12.530(3) Å, c = 8.432(1) Å, β = 91.75(2) Å, and Z = 4. The triclinic crystal B belongs to a P $\bar 1$ space group. The unit cell parameters are a = 11.386(2) Å, b = 12.326(2) Å, c = 12.411(3) Å, α = 83.07(1)°, β = 87.76(2)°, γ = 86.52(2)°, and Z = 4. The structure analyses show the title compound is the keto-form. Dimers in crystal packing of A and supramolecular one-dimensional (B) concatenate structures were assembled by the intermolecular hydrogen bonds.

  我们获得了一种新型吡唑酮衍生物 2-苯胺基-6H-5-(1-苯基-3-甲基-5-吡唑酮-4-亚烯)-1,3,4-噻二嗪（PMCP-PTSC），该衍生物含有 NNS 六原子杂环，并通过单晶 X 射线衍射、红外光谱和 1H NMR 光谱对其进行了表征。有趣的是，当从两种不同溶剂中生长时，会形成两种不同的晶体结构。单斜晶体 A 属于 P21/c 空间群。单胞参数为 a = 16.414(4) Å，b = 12.530(3) Å，c = 8.432(1) Å，β = 91.75(2) Å，Z = 4。三棱晶体 B 属于 P $\bar 1$ 空间群。单胞参数为 a = 11.386(2)埃，b = 12.326(2)埃，c = 12.411(3)埃，α = 83.07(1)°，β = 87.76(2)°，γ = 86.52(2)°，Z = 4。结构分析表明，标题化合物是酮基形式。通过分子间氢键的作用，形成了 A 晶体堆积中的二聚体和超分子一维（B）连接结构。