4-(4-fluorobenzoyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one | 129228-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-fluorobenzoyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 1-phenyl-3-methyl-4-(4-fluorobenzoyl)-5-pyrazolone；1-phenyl-3-methyl-4-p-fluorobenzoyl-pyrazol-5-one；PM4FBP；4-[(4-fluorophenyl)carbonyl]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one；4-(4-fluorobenzoyl)-5-methyl-2-phenyl-4H-pyrazol-3-one
• CAS: 129228-84-8
• 化学式: C₁₇H₁₃FN₂O₂
• 分子量: 296.301
• InChiKey: XGGBVDXMHJUCLX-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  491.6±35.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-fluorobenzoyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 以 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  镁配合物与NNO-三齿吡唑啉酸酯配体配合催化的丙交酯开环聚合

  摘要：

  一系列的镁benzylalkoxide络合物，[L Ñ的Mg（μ-OBN）] 2（1 - 14）由NNO-三齿配体pyrazolonate与各种吸电子供subsituents支持已被合成和表征。X射线晶体结构的研究表明，配合物1 - 3，5，7，9，和10是通过与五配位的金属中心benzylalkoxy氧原子的双核桥接。所有这些络合物都是L-丙交酯和rac开环聚合的有效引发剂丙交酯。根据动力学研究，这些金属配合物的活性受到苯环上带有给电子取代基的辅助配体的电子效应的显着影响，从而提高了聚合速率。此外，在少量引发剂的存在下，具有6的“活性”和“永生”特征为合成多达40根具有非常窄的多分散指数的聚丙交酯聚合物链铺平了道路。在所有镁配合物中，配合物6在0°C下对THF中的Pr含量高达88％的rac-丙交酯的开环聚合反应显示出最高的立体选择性。©2012 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.26426
• 作为产物：
  描述：

  苯肼 在 calcium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(4-fluorobenzoyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  镁配合物与NNO-三齿吡唑啉酸酯配体配合催化的丙交酯开环聚合

  摘要：

  一系列的镁benzylalkoxide络合物，[L Ñ的Mg（μ-OBN）] 2（1 - 14）由NNO-三齿配体pyrazolonate与各种吸电子供subsituents支持已被合成和表征。X射线晶体结构的研究表明，配合物1 - 3，5，7，9，和10是通过与五配位的金属中心benzylalkoxy氧原子的双核桥接。所有这些络合物都是L-丙交酯和rac开环聚合的有效引发剂丙交酯。根据动力学研究，这些金属配合物的活性受到苯环上带有给电子取代基的辅助配体的电子效应的显着影响，从而提高了聚合速率。此外，在少量引发剂的存在下，具有6的“活性”和“永生”特征为合成多达40根具有非常窄的多分散指数的聚丙交酯聚合物链铺平了道路。在所有镁配合物中，配合物6在0°C下对THF中的Pr含量高达88％的rac-丙交酯的开环聚合反应显示出最高的立体选择性。©2012 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.26426

文献信息

• Copper(<scp>ii</scp>) complexes with 4-acyl pyrazolone derivatives and diimine coligands: synthesis, structural characterization, DNA binding and antitumor activity
  作者：Jun Wang、Guan-Cheng Xu、Yan-Ping Zhang、Hua-Ying Luo、Jin-Yao Li、Li Zhang、Dian-Zeng Jia

  DOI：10.1039/c8nj02695e

  日期：——

  ability, followed by 2, 1 and H2L. Complexes 1–3 exhibit excellent cytotoxicity against cervical cancer HeLa cells and human esophageal cancer Eca-109 cells. Complex 3 displays the best activity for both cancer cell lines, and the IC50 values are 4.37 ± 0.08 μM and 3.68 ± 0.14 μM for HeLa and Eca-109 cells, respectively, which are about 13 times lower than that of the commercial antitumor drug cisplatin

  三种混合配体Cu（II）配合物[Cu（L）（bpy）]（1），[Cu（L）（phen）]（2）和[Cu（L）（dpq）]·CHCl 3（3）已经合成并充分表征，其中H 2 L = N-（1-苯基-3-甲基-4-（4-氟苯甲酰基）-5-吡唑啉酮）-2-水杨酰肼，bpy = 2,2'-联吡啶， phen = 1,10-菲咯啉，dpq =二吡咯并[3,2- d：2'，3'- f ]喹喔啉。单晶X射线衍射分析表明，配合物1-3具有单核结构，且Cu（II离子位于五坐标失真的方形金字塔形几何结构中。通过吸收滴定，溴化乙锭置换实验和电化学研究，研究了化合物与鲱鱼精子DNA的相互作用。所有化合物可以与DNA相互作用intercalatively和复杂3示出了最高的DNA结合能力，其次是2，1和^ h 2大号。配合物1-3对宫颈癌HeLa细胞和人食道癌Eca-109细胞具有优异的细胞毒性。复合物3对癌细胞系和IC
• Ring-opening polymerization of<scp>l</scp>-lactide catalyzed by calcium complexes
  作者：Mon-Wei Hsiao、Chu-Chieh Lin

  DOI：10.1039/c2dt32487c

  日期：——

  A series of calcium complexes supported by NNO-tridentate ketiminate ligands have been synthesized and characterized. X-ray structural studies indicate that these complexes bear a mononuclear feature with hexa-coordinated calcium centers bonding to two ketiminate ligands. Polymerization of L-lactide catalyzed by these complexes proceeds rapidly and well controlled in the presence of a variety of alcohols. In addition, these complexes reveal good catalytic activity even with the addition of up to 80 equiv. of benzyl alcohol as a transfer agent. Furthermore, kinetic studies show ROP of L-lactide is a first-order dependency on [LA] and a second-order dependency on [BnOH].

  我们合成并鉴定了一系列由 NNO-三叉酮亚胺配体支持的钙络合物。X 射线结构研究表明，这些配合物具有单核特征，六配位钙中心与两个酮亚胺配体成键。在这些配合物的催化下，L-内酰胺的聚合反应在多种醇类存在的情况下均能快速进行，且控制良好。此外，即使添加多达 80 等量的苯甲醇作为转移剂，这些复合物也能显示出良好的催化活性。此外，动力学研究表明，L-内酰胺的 ROP 与 [LA] 呈一阶依赖关系，与 [BnOH] 呈二阶依赖关系。
• Novel mixed ligand di-n-butyltin(IV) complexes derived from acylpyrazolones and fluorinated benzoic acids: Synthesis, characterization, cytotoxicity and the induction of apoptosis in Hela cancer cells
  作者：Bin Zhao、Xianmei Shang、Ling Xu、Wendian Zhang、Guangya Xiang

  DOI：10.1016/j.ejmech.2014.02.039

  日期：2014.4

  Twenty one novel mixed ligand di-n-butyltin(IV) complexes [(n)Bu(2)SnAL] (A = substituted 4-acyl-5-pyrazolone, and L = fluorinated benzoic acid) were prepared by condensation of di-n-butyltin(IV) oxide with HL and HA in 1:1:1 molar ratio in refluxing methanol. All of the complexes were characterized by elemental analyses, IR, NMR (H-1, C-13, Sn-119) and in four cases by X-ray diffraction. Cytotoxicity of the compounds was studied against two human cancer cell lines (KB and Hela) by means of the MU assay compared to cisplatin, featuring IC50 values in the low micromolar range. Hela cancer cell apoptosis-induced by 2 was examined by flow cytometry analysis, and preliminary results showed that 2 at concentrations of more than 1.0 mu M can induce apoptosis. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and characterization of some tin(II) and tin(IV) derivatives of 4-acyl-5-pyrazolones. Crystal structure of bis(1-phenyl-3-methyl-4-acetyl-pyrazolon-5-ato)tin(II)
  作者：Claudio Pettinari、Fabio Marchetti、Augusto Cingolani、Clara Marciante、Riccardo Spagna、Marcello Colapietro

  DOI：10.1016/s0277-5387(00)83014-4

  日期：1994.3

  Stable, four-coordinated (Q)2Sn compounds have been prepared, where QH is 1-phenyl-3-methyl-4-RC(=O)-pyrazol-5-one (R = CH3, CF3, n-C6H13, C6H5, p-F-C6H4, p-Cl-C6H4, p-Br-C6H4, p-I-C6H4, p-NO2-C6H4, p-CH3O-C6H4). They have been characterized through analytical data, IR and H-1, C-13 and Sn-119 NMR spectroscopy. In the crystal structure of the title compound (8), the tin atom is found in a distorted psi trigonal bipyramidal environment, with the tin lone pair occupying an equatorial site. The diaxial angle O-Sn-O is bent [149.8(2)2)degrees] and two sets of Sn-O distances are found [Sn-O(1) = 2.141 (5) angstrom; Sn-O(3) = 2.133 (5) angstrom; Sn-O(2) = 2.296 (6) angstrom; Sn-O(4) = 2.313 (6) angstrom. Oxidative addition of iodomethane or dihalogens (Br2 or I2) to (Q)2Sn provides a route to new (Q)2R(n)Sn(IV)X2-n compounds (where X = Br or I; R = CH3 or X).
• Ring-opening polymerization of lactides catalyzed by magnesium complexes coordinated with NNO-tridentate pyrazolonate ligands
  作者：Hui-Ju Chuang、Hsiao-Li Chen、Jian-Li Ye、Zn-Yun Chen、Pei-Ling Huang、Tzu-Ting Liao、Tsung-En Tsai、Chu-Chieh Lin

  DOI：10.1002/pola.26426

  日期：2013.2.1

  these complexes acted as efficient initiators for the ring‐opening polymerization of L‐lactide and rac‐lactide. Based on kinetic studies, the activity of these metal complexes is significantly influenced by the electronic effect of the ancillary ligands with the electron‐donating substituents at the phenyl rings enhancing the polymerization rate. In addition, the “living” and “immortal” character of 6 has

  一系列的镁benzylalkoxide络合物，[L Ñ的Mg（μ-OBN）] 2（1 - 14）由NNO-三齿配体pyrazolonate与各种吸电子供subsituents支持已被合成和表征。X射线晶体结构的研究表明，配合物1 - 3，5，7，9，和10是通过与五配位的金属中心benzylalkoxy氧原子的双核桥接。所有这些络合物都是L-丙交酯和rac开环聚合的有效引发剂丙交酯。根据动力学研究，这些金属配合物的活性受到苯环上带有给电子取代基的辅助配体的电子效应的显着影响，从而提高了聚合速率。此外，在少量引发剂的存在下，具有6的“活性”和“永生”特征为合成多达40根具有非常窄的多分散指数的聚丙交酯聚合物链铺平了道路。在所有镁配合物中，配合物6在0°C下对THF中的Pr含量高达88％的rac-丙交酯的开环聚合反应显示出最高的立体选择性。©2012 Wiley Periodicals，Inc