4-(呋喃-2-羰基)-5-甲基-2-苯基-4H-吡唑-3-酮 | 189090-94-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(呋喃-2-羰基)-5-甲基-2-苯基-4H-吡唑-3-酮
• 英文名称: 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone
• 英文别名: 1-phenyl-3-methyl-4-(2-furoyl)-pyrazole-5-one；1-phenyl-3-methyl-4-(α-furoyl)-5-pyrazolone；4-(furan-2-carbonyl)-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one；1-phenyl-3-methyl-4-furylpyrazol-5-one；4-furancarbonyl-3-methyl-1-phenylpyrazol-5-one；4-(Furan-2-carbonyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one；4-(furan-2-carbonyl)-5-methyl-2-phenyl-4H-pyrazol-3-one
• CAS: 189090-94-6
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: AMSWNUWFGDJHEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲基氨基硫脲 、 4-(呋喃-2-羰基)-5-甲基-2-苯基-4H-吡唑-3-酮 以 甲醇 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  Solid-state proton transfer studies on phototautomerization of 1-phenyl-3-methyl-4-furoyl-5-pyrazolone 4-methyl thiosemicarbazone

  摘要：

  A novel keto-enol phototautomeric compound of 1-phenyl-3-methyl-4-(-furoyl)-5-pyrazolone 4-methyl thiosemicarbazone was found to undergo phototautomerization in the crystalline state, The reaction rate constant was studied based on the first-order kinetics curve. Crystal structural analysis and theoretical calculations show that the pyrazolone ring stabilizes in the keto form. The conclusion can be made that its phototautomerization in the crystalline state is associated with a photo-induced intermolecular double-proton-transfer reaction along intermolecular hydrogen bonds N-(HO)-O-... and (SH)-H-...-N leading to a colored tautomer as the compound crystallizes in a hydrogen bonded supramolecular configuration. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2006.06.115
• 作为产物：
  描述：

  呋喃甲酰氯 、 依达拉奉 在 calcium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.5h， 生成 4-(呋喃-2-羰基)-5-甲基-2-苯基-4H-吡唑-3-酮
  参考文献：
  名称：

  Inhibitory effect of β-diketones and their metal complexes on TNF-α induced expression of ICAM-1 on human endothelial cells

  摘要：

  Recent reports show that the natural beta-diketone curcumin displays important biological properties regarding the intercellular adhesion molecule-1 (ICAM-1), which plays a critical role in the immune responses and inflammation. In this study the ICAM-1 inhibitory activity of beta-diketone compounds, which are curcumin models lacking aromatic peripheral hydroxyl and methoxy groups, along with some metal derivatives is investigated. beta-Diketones are systematically more active than metal complexes and the best obtained inhibition is 75% for both groups. The best inhibitors are 4-benzoyl-3-methyl-1-phenyl-pyrazol- 5-one (HQ(Ph)) among the ligands, and sodium benzoylacetonato among metal derivatives. These results appear in line with the reported antitumor activity of related species. Since 4-acyl-5-pyrazolones posses four tautomeric forms, those corresponding to HQ(Ph) were investigated using density functional theory. Docking of all HQ(Ph) tautomers on ICAM-1 protein was performed suggesting one keto-enol form favored to act in biological environment. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.064

文献信息

• 一种吡唑啉酮氧钒配合物及其制备方法和应 用以及所述吡唑啉酮氧钒配合物的单晶制备
  申请人：河北民族师范学院

  公开号：CN110218224B

  公开（公告）日：2021-12-31

  本发明属于有机配合物的技术领域。本发明提供了一种吡唑啉酮氧钒配合物。本发明所述吡唑啉酮氧钒配合物上有两个乙醇分子参与配位，提高了其水溶性。而一般的氨基酸或水杨醛类希夫碱氧钒类配合物的水溶性都相对较低，本发明得到的吡唑啉酮氧钒配合物地高水溶性使得其抗PTP1B酶的活性大大提高，可达92%。本发明还提供了所述吡唑啉酮氧钒配合物的制备方法以及所述吡唑啉酮氧钒配合物的单晶制备方法。本发明提供的合成方法操作极其简单，具有普适性，适于批量生产。本发明还提供所述吡唑啉酮氧钒配合物在制备治疗糖尿病药物中的应用，为糖尿病的治愈提供了新的希望。
• Synthesis, crystal structure, and electrocatalytic behavior of a zinc(II) complex derived from a heterocyclic acylpyrazolone
  作者：Xiao-Zhe Pang、Jin-Zhou Li、Li-Sheng Chen、Heng-Qiang Zhang

  DOI：10.1080/00958972.2013.771775

  日期：2013.3.1

  a slightly distorted octahedral structure, Zn2+ is located at an inversion center from four oxygens, two of ligands in the equatorial plane, two methanols axial. The complex has a two-dimensional supramolecular structure connected by O–H N bonding interactions. In the CV, one oxidation peak of adenine with E p = 1.018 V in pH = 7.0 shows that the [Zn(PMαFP)2(CH3OH)2]/glassy carbon modified electrode

  合成了酰基吡唑啉酮复合物 [Zn(PMαFP)2(CH3OH)2]（HPMαFP = 1-苯基-3-甲基-4-（α-呋喃酰基）-5-吡唑啉酮）。通过单晶 X 射线衍射、IR、UV、荧光光谱、DTA-TG 和循环伏安法 (CV) 对该配合物进行了表征。结构是正交的，pbca 组，具有单元参数：a = 15.015(3) Å，b = 9.844(2) Å，c = 20.663(4) Å，Z = 4，S = 1.025，R 1 = 0.0353 和 wR 2 = 0.0924。该配合物显示出略微扭曲的八面体结构，Zn2+ 位于四个氧的反转中心，两个配体在赤道面，两个甲醇为轴向。该复合物具有通过 O-HN 键相互作用连接的二维超分子结构。在 CV 中，一个腺嘌呤氧化峰在 pH = 7 时具有 E p = 1.018 V。
• The reactivity of new (1,5-cyclooctadiene)rhodium acylpyrazolonates towards N- and P-donor ligands: X-ray structures of [Rh(1,5-COD)Qs], [Rh(1,5-COD)(phen)]Qs·0.5H2O (HQs=1-phenyl-3-methyl-4-(2-thenoyl)-pyrazol-5-one) and [Rh(1,5-COD)Br]2
  作者：Claudio Pettinari、Fabio Marchetti、Augusto Cingolani、Gianluca Bianchini、Andrei Drozdov、Vyacheslav Vertlib、Sergei Troyanov

  DOI：10.1016/s0022-328x(02)01122-1

  日期：2002.5

  Complexes [Rh(1,5-COD)(Q)] have been prepared by the reaction between [Rh(1,5-COD)Cl](2) (1,5-COD = 1,5-cyclooetadiene) and HQ (where HQ = 1-phenyl-3-methyl-4-R-pyrazol-5-one: R = 2-thenoyl (HQ(s)), 2-furanoyl (HQ(o)) or tert-butylacetyl (HQ(T)). [Rh(1,5-COD)(Q)] react with N-2-donor ligands such as 1,10-phenanthroline (phen) or 2,2-bipyridyl (bipy) yielding ionic compounds [Rh(1,5-COD)(N-2-donor)]Q. The substitutional lability of 1,5-COD in [Rh(1,5-COD)(Q)] versus mono- and di-organophosphine ligands was also investigated. In all cases 1,5-COD has been displaced. Reaction with two equivalents of PPh3 gave, upon oxidation of the Rh(l) centre, [Rh(PPh3)1(01)(Q)l species containing a eta(2)-peroxo-group. Reaction of [Rh(1,5-COD)(Q)] with the chelating P-2-donor 1,2-bis(diphenylphosphino)ethane (dppe) or 4,4'-bis(diphenylphosphino)ferrocene (dppf) yields the peroxo Rh(III) compounds [Rh(dppe)(2)O-2]Q(T) and [Rh(dppf)O-2(Q(T))] or Rh(I) species [Rh(dppf-O-2)(Q(T))] containing the diphosphine in the oxidised form. Finally the reaction between [Rh(1,5-COD)(Q)] and allylbromide yields the well-known [Rh(1,5-COD)Br](2). All complexes have been characterised by analytical and spectral data (IR, H-1 and P-31 ((1)HJ-NMR spectra). The crystal structures of [Rh(1,5-COD)(Q(5))], [Rh(1,5-COD)(phen)]Q(5) and [Rh(1,5-COD)Br](2), all containing a Rh(l) atom in a square coordinate environment, are also reported. (C) 2002 Elsevier Science B.V. All rights reserved.
• Copper(I) monophosphine complexes with functionalized acylpyrazolonate ligands: Syntheses of heterobimetallic Cu–Zn and Cu–Ru adducts
  作者：Augusto Cingolani、Fabio Marchetti、Claudio Pettinari、Riccardo Pettinari、Brian W. Skelton、Neil Somers、Allan H. White

  DOI：10.1016/j.poly.2005.07.020

  日期：2006.1

  Copper(I) acylpyrazolonate derivatives of formula [Cu(Q)(PPh3)(2)] (HQ = HQ(C2F5) = 1-phenyl-3-methyl4-pentafluoropropanoyl-pyrazol-5-one, HQ(CF3,CF3) = 1-(4-trifluoromethyl)phenyl-3-methyl-4-trifluoroacetylpyrazol-5-one, HQ(naph) = 1-phenyl-3-methyl-4-(1-naphthoyl)pyrazol-5-one, HQ(fur) = 1-phenyl-3-methyl-4-furylpyrazol-5-one, HQ(thi) = 1-phenyl-3-methyl-4-thienoylpyrazol-5-one, HQ(CF3,py) = 1-(2-pyridyl)-3-methyl-4-trifluoromethylpyrazol-5-one) have been synthesized and characterized, both in the solid state and in solution. The isomorphous crystal structures of [Cu(Q(fur))(PPh3)(2)] and [Cu(Q(thi))(PPh3)(2)] and of [CU(Q(C2F5))(PPh3)(2)] show their copper atoms in distorted tetrahedral environments. Apart from the derivative [Cu(Q(naph))(PPh3)(2)] they are fluxional in chloroform solution, dissociating partially to the [Cu(Q)(PR3)] fragment and free PR3, or existing in solution as [Cu(O-2-Q)(PR3)(2)] or [Cu(O-Q)(PR3)(2)] species, with CuO2P2 or CuOP2, metal environments, in equilibrium with each other. By contrast, in [Cu(Q(CF3,py))(PPh3)(2)] the Q(CF3.py) ligand is coordinated to copper through the nitrogen atoms of the pyrazole and pyridine rings. The latter compound reacts with Zn(BF4)(2)center dot xH(2)O and [Ru(p-cymene)Cl-2](2) affording ionic heterobimetallic adducts. (c) 2005 Elsevier Ltd. All rights reserved.