2-(4-methoxyphenyl)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one | 338422-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-methoxyphenyl)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 1-(4-methoxylbenzyl)-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one；2-(4-methoxyphenyl)-5-(trifluoromethyl)-4H-pyrazol-3-one
• CAS: 338422-68-7
• 化学式: C₁₁H₉F₃N₂O₂
• mdl: MFCD00664204
• 分子量: 258.2
• InChiKey: PVFOLBVIPYACQR-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±42.0 °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：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one 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91%的产率得到4-diazo-1-(4-methoxyphenyl)-3-trifluoromethylpyrazolin-5-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：

  4-甲氧基苯肼盐酸盐 、 三氟乙酰乙酸乙酯 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 2-(4-methoxyphenyl)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  Novel hybrids of 3-n-butylphthalide and edaravone: Design, synthesis and evaluations as potential anti-ischemic stroke agents

  摘要：

  Fourteen hybrids (10a-g, 11a-g) of 3-n-butylphthalide (NBP) and edaravone (Eda) analogues have been designed and synthesized as potential anti-ischemic stroke agents. In vitro biological studies showed that compounds 10d and 10g exhibited more potent anti-platelet aggregation than ticlopidine (Ticlid), aspirin (ASP) and NBP. Compound 10g more significantly prevented H2O2-mediated neuronal cell (PC12) death than NBP, Eda or NBP together with Eda. Meanwhile, 10g also possessed potent radical scavenging effects on hydroxyl radical ((OH)-O-center dot) and superoxide anion radical (O-center dot(2)-). Our findings may provide new insights into the development of these hybrids, like 10g, for the intervention of ischemic stroke. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.090

文献信息

• SO₂F₂ mediated transformation of pyrazolones into pyrazolyl fluorosulfates
  作者：Jing Leng、Hua-Li Qin

  DOI：10.1039/c9ob00903e

  日期：——

  The construction of a class of novel N-heterocyclic molecules containing both pyrazole and fluorosulfate functionalities was achieved through the reactions of pyrazolones with SO2F2 in good to excellent yields. The fluorosulfate moieties were utilized as versatile building blocks in the Suzuki coupling reaction and SuFEx click chemistry.

  通过吡唑啉酮与SO 2 F 2的反应，以良好至极好的收率，可以实现一类同时具有吡唑和氟硫酸盐官能团的新型N-杂环分子的构建。在Suzuki偶联反应和SuFEx click化学中，氟代硫酸盐部分被用作通用的结构单元。
• A consecutive one-pot two-step approach to trifluoromethylated pyrazolo[4ʹ,3ʹ:5,6]pyrano[2,3-b]indoles promoted by molecular iodine
  作者：Yingjun Zhu、Fanhui Chen、Yidi Zhou、Zhangping Kang、Min Zhang、Hongmei Deng、Liping Song

  DOI：10.1016/j.jfluchem.2018.04.016

  日期：2018.7

  An one-pot two-step three-component reaction of 2-indolinone, aromatic aldehydes and 1-aryl-3-trifluoromethyl-5-pyrazolone afforded trifluoromethylated poly-heterocyclic compounds containing pyrazolo[4ʹ,3ʹ:5,6]pyrano[2,3-b]indole skeleton. This atom economic and facile manipulative reaction involved initial treatment of three-component reaction mixtures with molecular iodine, followed by intramolecular

  一锅二步，由2-吲哚酮，芳族醛和1-芳基-3-三氟甲基-5-吡唑啉酮进行三步反应，得到含吡唑并[4ʹ，3ʹ：5,6]吡喃并[2]的三氟甲基化多杂环化合物。 ，3-b]吲哚骨架。这种原子经济且操作简便的反应涉及用分子碘对三组分反应混合物进行初始处理，然后与POCl 3进行分子内环化反应，而无需分离即可一锅法进行。与逐步反应相比，获得了更连续的三氟甲基吡唑并[4，3，5：6]吡喃并[2，3-b]吲哚的方法。
• A facile and consecutive approach to trifluoromethylated spirochromeno[2,3-c]-6H-Pyrazol-2′,5-dione derivatives
  作者：Zhangping Kang、Yang Wang、Lu Zhou、Min Zhang、Liping Song、Hongmei Deng

  DOI：10.1016/j.jfluchem.2016.06.020

  日期：2016.8

  A facile and consecutive one-pot, multi-component reaction for synthesis of trifluoromethylated spirochromeno[2,3-c]-6H-pyrazol-2′,5-dione derivatives by the reaction of isatin, cyclohexane-1,3-dione and 1-aryl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one in the presence of p- toluenesulfonic acid (p-TSA) with good yields was reported. Compared with the stepwise reactions, the p-TSA played dual roles as

  靛红与环己烷-1,3-二酮反应合成三氟甲基化螺环色素[2,3- c ] -6 H-吡唑-2'，5-二酮衍生物的简便且连续的多组分反应报道了在对甲苯磺酸（p -TSA）存在下1-芳基-3-（三氟甲基）-1 H-吡唑-5（4 H）-一，收率良好。与逐步反应相比，p -TSA在转化过程中既起催化剂作用，又起脱水剂的作用。通过光谱法和X射线衍射分析确定新化合物的结构。此外，化合物5形成的可能机理 被提出。
• 并环吡唑啉酮衍生物及其制备方法
  申请人：安徽师范大学

  公开号：CN111269235A

  公开（公告）日：2020-06-12

  本发明涉及有机合成领域，公开了一种并环吡唑啉酮衍生物及其制备方法，所述制备方法包括：(1)将[Cp*IrCl2]2、AgOAc、吡唑啉酮类化合物、叠氮化合物和溶剂混合反应；(2)经TLC跟踪反应和柱色谱分离得到并环吡唑啉酮衍生物。该制备方法具有原料易得、稳定性高、产率高、反应条件简单等优点。
• Synthesis of 4‐Alkenylated Pyrazolinones by 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)‐Mediated Oxidative Coupling Reaction
  作者：Yuhui Tao、Huafang Gu、Hongshuang Xia、Hongjiao Yang、Jinghua Li、Xiaoliang Xu、Dongping Cheng

  DOI：10.1002/ejoc.202201480

  日期：2023.2.13

  Synthesis of 4-alkenylated pyrazolinones derivatives by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of 1,3-diarylpropenes with pyrazolinones. The methodology has the advantages of metal-free, one-pot, high atom economy, and mild condition.

  通过 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 介导的 1,3-二芳基丙烯与吡唑啉酮的氧化偶联反应合成 4-烯基化吡唑啉酮衍生物。该方法具有无金属、一锅法、原子经济性高、条件温和等优点。