1-phenyl-3-methyl-4-(tert-butylacetyl)-5-pyrazolone | 216253-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1-phenyl-3-methyl-4-(tert-butylacetyl)-5-pyrazolone
• 英文别名: 1-phenyl-3-methyl-4-neopentylcarbonylpyrazol-5-one；1-phenyl-3-methyl-4-tert-butylacetyl-pyrazol-5-one；4-tert-butylacetyl-3-methyl-1-phenylpyrazol-5-one；4-(3,3-dimethylbutanoyl)-5-methyl-2-phenyl-4H-pyrazol-3-one
• CAS: 216253-66-6
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: RRHQLAXVILJEKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-methyl-4-(tert-butylacetyl)-5-pyrazolone 在 calcium chloride 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以84%的产率得到bis(4-t-butylacetyl-3-methyl-1-phenylpyrazol-5-onato)bis(ethanol)calcium(II)
  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
• 作为产物：
  描述：

  3,3-二甲基丁酰氯 、 依达拉奉 以 1,4-二氧六环 为溶剂， 生成 1-phenyl-3-methyl-4-(tert-butylacetyl)-5-pyrazolone
  参考文献：
  名称：

  具有酰基吡唑啉酮和含磷配体的混合配体镧系元素络合物

  摘要：

  用量子化学方法对乙酰丙酮镧与各种含磷农药，有毒气体及其水解产物的反应进行了建模。在大多数情况下，有机磷化合物取代水的焓为负。在使用乙酸乙酯（二乙氧基磷酰基）乙酸乙酯作为模型化合物的溶液中研究复合物。合成了具有酰基吡唑啉酮和乙酸乙酯（二乙氧基磷酰基）的混合配体镧系元素络合物。确定for络合物的晶体结构。

  DOI：

  10.1134/s1070328413030020

文献信息

• Electroluminescent materials and devices
  申请人：Kathirgamanathan Poopathy

  公开号：US20070259208A1

  公开（公告）日：2007-11-08

  An electroluminescent composition is provided comprising: (a) a compound of the general chemical formula (I): wherein M is lithium, sodium, potassium, rubidium, caesium, beryllium, magnesium, calcium, strontium, barium, copper, silver, gold, zinc, boron, aluminum, gallium, indium, germanium, tin, antimony, lead, manganese, iron, ruthenium, osmium, cobalt, rhodium, iridium, nickel, palladium, platinum, cadmium or chromium; n is the valence of M; and R 1 , R 2 and R 3 can be the same or different, and are selected from hydrogen, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aromatic, heterocyclic or polycyclic ring structure, a fluorocarbon, a halogen or a nitrile group; and (b) a suitable dopant. The composition may be used in forming electroluminescent devices.

  提供了一种电致发光组合物，包括：（a）一种具有一般化学式（I）的化合物：其中M是锂、钠、钾、铷、铯、铍、镁、钙、锶、钡、铜、银、金、锌、硼、铝、镓、铟、锗、锡、锑、铅、锰、铁、钌、铑、铱、镍、钯、铂、镉或铬；n是M的价；R1、R2和R3可以相同也可以不同，并且选择自氢、取代或未取代的脂肪基、取代或未取代的芳香、杂环或多环环状结构、氟碳化合物、卤素或腈基；以及（b）适当的掺杂剂。该组合物可用于制造电致发光器件。
• Marchetti, Fabio; Pettinari, Claudio; Cingolani, Augusto, Journal of the Chemical Society, Dalton Transactions, 1998, # 19, p. 3325 - 3333
  作者：Marchetti, Fabio、Pettinari, Claudio、Cingolani, Augusto、Leonesi, Dante、Drozdov, Andrei、Troyanov, Sergei I.

  DOI：——

  日期：——
• The Effect of Different Neutral Ligands on Photoluminescence and Electroluminescence Properties of Ternary Terbium Complexes
  作者：Hao Xin、Mei Shi、Xi Cun Gao、Yan Yi Huang、Ze Liang Gong、Dao Bo Nie、Hong Cao、Zu Qiang Bian、Fu You Li、Chun Hui Huang

  DOI：10.1021/jp037816h

  日期：2004.7.1

  Three terbium complexes Tb(tba-PMP)(3)(TPPO) (A), Tb(tba-PMP)(3)(H2O) (B), and Tb(tba-PMP)(3)(Phen) (C) (where tba-PMP, TPPO, and Phen stand for beta-diketone 1-phenyl-3-methyl-4-(tert-butylacetyl)-5-pyrazolone, triphenyl phosphine oxide, and 1,10-phenanthroline, respectively) with different neutral ligands were synthesized and characterized, and the mechanism of how the neutral ligands affect photoluminescence (PL) and electroluminescence (EL) properties of terbium complexes was studied. Experiments revealed neutral ligand TPPO and Phen strongly affect the terbium complex PL intensity, TPPO enhanced the PL intensity of complex A, while Phen reduced the PL intensity of complex C compared to that of complex B. Investigation indicated this is caused by the different excited energy levels between tba-PMP, TPPO, and Phen, which were obtained from their phosphorescence spectra measured with their corresponding gadolinium complexes Gd(tba-PMP)(3)(H2O)(EtOH), Gd(TPPO)(2)(NO3)(3), and Gd(Phen)(2)(NO3)(3), Compared to complex B, the energy absorbed by TPPO can be efficiently transferred to tba-PMP and the central ion Tb3+ due to its excited singlet and triplet energy levels matching that of tba-PMP and the D-5(4) energy level of Tb3+, and consequently enhancing the PL intensity of A, while on the contrary, negative energy transfer occurred between Phen and tab-PMP or Tb3+ since the triplet energy level of Phen is lower than that of tba-PMP and the D-5(4) energy level of Tb3+ as well. Experimental results show terbium complex electroluminescence (EL) is greatly dependent on its PL intensity, the performance achieved based on complexes A, B, and C being 9540 cd/m(2) and 7.2 lm/W, 3230 cd/m(2) and 1. 17 lm/W, and 690 cd/m(2) and 0.13 lm/W, respectively, with the power efficiency ratio A:B:C 55:9:1, which was greatly enlarged compared to their PL intensity ratio A:B:C = 2.1:1.3:1.
• Synthesis, Molecular Structure (X-ray and DFT), and Solution Behavior of Titanium 4-Acyl-5-pyrazolonates. Correlations with Related Antitumor β-Diketonato Derivatives
  作者：Francesco Caruso、Claudio Pettinari、Fabio Marchetti、Paolo Natanti、Christine Phillips、Joseph Tanski、Miriam Rossi

  DOI：10.1021/ic700935x

  日期：2007.9.1

  Previously reported structure-activity relationships have shown two features for effective antitumor activity of titanium beta-diketone complexes: (a) ligand asymmetry and (b) the presence of planar substitutents on the ligand. Mono- and dinuclear derivatives, studied with diffraction and DFT methods show that (a) is consistent with different Ti-O(beta-diketonato) bond lengths, which are longer than Ti-O(oxo) and Ti-O(alkoxy) ones. pi-pi features observed in dinuclear derivatives correlate with strong reactivity of related complexes with DNA and support DNA intercalation by such planar groups, in agreement with (b). Large variation for Ti-O bond lengths and Ti-O-C bond angles in the ethoxy moiety is associated with the titanium withdrawing effect and oxygen bonding s character; it is confirmed through exploration of the Cambridge crystallographic database. This ethoxy geometrical flexibility also suggests versatile accommodation in protein pockets and/or other biological targets. Electrospray ionization mass spectrometry (ESI-MS) spectra show formation of di- and trinuclear Ti-4-acyl-5-pyrazolonato cationic oligomers. Hydrolysis/oligomerization is also described by NMR results.
• US7211334B2
  申请人：——

  公开号：US7211334B2

  公开（公告）日：2007-05-01