1-苯基-3-三氟甲基-1(H)-吡唑-5-酮 | 321-07-3

• 物质功能分类: 有机原料 - 有机氟化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 1-苯基-3-三氟甲基-1(H)-吡唑-5-酮
• 中文别名: 1-苯基-3-三氟甲基-2-吡唑啉-5-酮
• 英文名称: 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one
• 英文别名: 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one；1-phenyl-3-trifluoromethyl-5-pyrazolone；1-Phenyl-3-(trifluoromethyl)-2-pyrazolin-5-one；2-phenyl-5-(trifluoromethyl)-4H-pyrazol-3-one
• CAS: 321-07-3
• 化学式: C₁₀H₇F₃N₂O
• mdl: MFCD00051655
• 分子量: 228.174
• InChiKey: GLGRRRKQSFURGD-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196°C
• 沸点：
  278.7±40.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1-苯基-3-三氟甲基-1(H)-吡唑-5-酮 在 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  1,3-Dipolar cycloaddition reaction of 3-trifluoromethyl-4-diazopyrazolinones with acetylenedicarboxylates

  摘要：

  Refluxing of 3-trifluoromethyl-4-diazopyrazolinones 1 with dimethyl acetylenedicarboxylates 2 in toluene for 48 h afforded trifluoromethyl-substituted pyrazolo [1,5-d][1,2,4]triazin-7-ones, which resulted from the [3+2] dipolar cycloaddition followed by a rearrangement of the initially produced spiro 3H-pyrazole adducts. However, when 1 was heated to 160 degrees C in dichlorobenzene (o-DCB) for 8 h, it lost nitrogen and reacted with 2 to give 3-trifluoromethyl furo[2,3-c]pyrazoles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.062
• 作为产物：
  描述：

  5-ethoxy-1-phenyl-3-trifluoromethyl-1H-pyrazole 在 水 、 氢溴酸 作用下， 反应 4.0h， 以85%的产率得到1-苯基-3-三氟甲基-1(H)-吡唑-5-酮
  参考文献：
  名称：

  Nitrogen's reactivity of various 3-alkoxypyrazoles

  摘要：

  Our current interest in the design of original chemical libraries featuring a pyrazole nucleus led us to focus on the chemistry of the 3-alkoxy-5-methylpyrazoles we have recently made readily available. With in mind the preparation of an array of the less accessible 1-arylpyrazol-3-ones, the present report describes the respective nitrogen's reactivity of various 3-alkoxypyrazoles toward arylation reaction, using arylboronic acids, as well as alkylation reactions using methyl iodide or benzylbromide. The structure assignments of the isomers obtained were achieved using long distance N-15-H-1 NMR correlation measurements or by the recourse to unambiguous synthetic pathways. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.099

文献信息

• Discovery of pyrazolone spirocyclohexadienone derivatives with potent antitumor activity
  作者：Lei Wang、Zixuan Yang、Tianyu Ni、Wencai Shi、Yunbo Guo、Keliang Li、Anzhe Shi、Shanchao Wu、Chunquan Sheng

  DOI：10.1016/j.bmcl.2019.126662

  日期：2020.1

  Starting from easy accessible pyrazoletetrahydropyran acetals, a series of new pyrazolone spirocyclohexadienone derivatives were synthesized and assayed for antitumor activity. Compound 10s was identified to possess good antitumor activity. It could induce MDA-MB-231 cancer cell apoptosis in a concentration dependent manner and arrest the cell cycle progression mainly at the G1 phase.

  从易于获得的吡唑四氢吡喃缩醛开始，合成了一系列新的吡唑啉酮螺环己二酮衍生物，并测定了其抗肿瘤活性。鉴定出化合物10s具有良好的抗肿瘤活性。它可以以浓度依赖的方式诱导MDA-MB-231癌细胞凋亡，并主要在G1期阻止细胞周期进程。
• A simple and catalyst free one pot access to the pyrazolone fused 2,8-dioxabicyclo[3.3.1]nonanes
  作者：Chiranjeevi Bingi、Narender Reddy Emmadi、Madhu Chennapuram、Jagadeesh Babu Nanubolu、Krishnaiah Atmakur

  DOI：10.1039/c4ra07278b

  日期：——

  Synthesis of a series of novel aryl and heteroaryl fused 2,8-dioxabicyclo[3.3.1]nonanes (3) was accomplished by one pot, catalyst free reaction of 2-hydroxy chalcone (1) with 3-trifluoromethyl substituted pyrazolone (2) in xylene at reflux temperature. The role of the trifluoromethyl functional group in formation of 3 was confirmed by comparative studies with 3-methyl substituted pyrazolones (2c,d)

  通过一锅，2-羟基查耳酮（1）与3-三氟甲基取代的吡唑酮（2）的无催化剂反应，完成了一系列新颖的芳基和杂芳基稠合的2,8-二氧杂双环[3.3.1]壬烷（3）的合成。在回流温度下在二甲苯中。通过与3-甲基取代的吡唑啉酮（2c，d）的比较研究证实了三氟甲基官能团在3的形成中的作用，并给出了结果。
• Facile synthesis of fused polyheterocycles containing trifluromethylated benzo[6,7]chromeno[2,3-c]pyrazoles via one-pot two-step MCRs
  作者：Wenwen Duan、Zeyu Li、Fanhui Chen、Min Zhang、Hongmei Deng、Liping Song

  DOI：10.1016/j.jfluchem.2020.109525

  日期：2020.7

  polyheterocyclic products trifluoromethylated benzo[6,7]chromeno[2,3-c]pyrazole-5,10-dione derivatives. Furthermore, an efficient, straightforward protocol has been developed for the synthesis of trifluoromethylated benzo[6,7]chromeno[2,3-c]pyrazole-5,10-dione derivatives at medium yields via one-pot, two-step, three-component reactions. Meanwhile, the structures of typical products were further confirmed by XRD-analysis

  通过NH 4 OAc催化的2-羟基-1,4-萘醌，芳香醛和三元醇的一锅，三组分反应，在乙腈溶剂中高收率合成了一系列非环状产物：三氟甲基吡唑啉酮系链的三取代甲烷衍生物。1-芳基-3-三氟甲基-5-吡唑酮。用脱水剂SOCl 2 /吡啶在乙腈中处理三氟甲基吡唑啉酮连接的三取代甲烷衍生物，得到相应的环合稠合多杂环产物，三氟甲基化苯并[6,7] chromeno [2,3 - c ]吡唑-5,10-二酮衍生物。此外，已经开发了一种有效，简单的方法来合成三氟甲基化的苯并[6,7]铬[2,3- c一锅，两步，三组分反应以中等收率得到]吡唑-5,10-二酮衍生物。同时，通过XRD分析进一步证实了典型产品的结构。
• Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions
  作者：Yong Yuan、Liang-Sen Li、Lin Zhang、Feng Wang、Lin Jiang、Lin Zuo、Qi Wang、Jian-Guo Hu、Aiwen Lei

  DOI：10.1039/d1cc00486g

  日期：——

  An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product

  已经开发了2.5-取代的吡唑啉-5-酮与硫氰酸铵之间的电化学氧化交叉偶联反应，从而在金属催化剂，外源氧化剂和外源电解质-的作用下产生了一系列前所未有的交叉偶联产物。免费条件。值得注意的是，由于所得的交叉偶联产物几乎不溶于MeCN，因此无需硅胶柱纯化即可提供纯产物。此外，制备的氧化铵是用于合成官能化吡唑衍生物的通用构建基。
• [EN] PYRAZOLONE DERIVATIVES AS NITROXYL DONORS<br/>[FR] DÉRIVÉS DE PYRAZOLONE UTILISÉS EN TANT QUE DONNEURS DE NITROXYLE
  申请人：CARDIOXYL PHARMACEUTICALS INC

  公开号：WO2015183839A1

  公开（公告）日：2015-12-03

  The disclosed subject matter provides pyrazolone derivative compounds, pharmaceutical compositions comprising such compounds, kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  所披露的主题提供了吡唑酮衍生物化合物，包括这些化合物的药物组合物，包括这些化合物的试剂盒，以及使用这些化合物或药物组合物的方法。具体而言，所披露的主题提供了使用这些化合物或药物组合物治疗心力衰竭的方法。