2-p-Tolyl-5-trifluoromethyl-2,4-dihydro-pyrazol-3-one | 63695-47-6

• 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-p-Tolyl-5-trifluoromethyl-2,4-dihydro-pyrazol-3-one
• 英文别名: 2-(4-methylphenyl)-5-(trifluoromethyl)-4H-pyrazol-3-one
• CAS: 63695-47-6
• 化学式: C₁₁H₉F₃N₂O
• mdl: MFCD00215510
• 分子量: 242.2
• InChiKey: IJXZPNBQRFQWPE-UHFFFAOYSA-N

物化性质

• 沸点：
  312.8±42.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-p-Tolyl-5-trifluoromethyl-2,4-dihydro-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 、 邻二氯苯 为溶剂， 反应 7.0h， 生成 dimethyl 1-(p-tolyl)-3-(trifluoromethyl)-1H-furo[2,3-c]pyrazole-4,5-dicarboxylate
  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-p-Tolyl-5-trifluoromethyl-2,4-dihydro-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

• CuI-catalyzed sulfenylation of 1-aryl trifluoromethyl pyrazolones: Direct formation of C-S-C bond using aryl iodides and carbon disulfide
  作者：Vaibhav D. Prajapati、Ronak V. Prajapati、Vishal B. Purohit、Jemin R. Avalani、Ronak D. Kamani、Nirav H. Sapariya、Dipak K. Raval

  DOI：10.1016/j.jfluchem.2021.109920

  日期：2022.1

  A novel approach for CuI-catalyzed sulfenylation of 1-aryl-3-trifluoromethyl pyrazolones (2a-d) with aryl iodides (1a-j) and carbon disulfide as sulfenylating agent has been described. The protocol was found to be simple and efficient benign to access a broad array of fluorinated sulfenyl pyrazolones in good yields. The formation of C-S-C bond was achieved by using inexpensive and readily available

  已经描述了一种用芳基碘化物(1a-j)和二硫化碳作为亚磺酰化剂对 1-芳基-3-三氟甲基吡唑啉酮(2a-d)进行 CuI 催化亚磺酰化的新方法。发现该方案简单有效，可以以良好的收率获得广泛的氟化亚磺基吡唑啉酮。CSC 键的形成是通过使用廉价且容易获得的起始材料来实现的。
• 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。
• Transition-metal-free direct arylselenation of 1-aryl-3-methyl pyrazolones using diselenides
  作者：Vaibhav D. Prajapati、Ronak V. Prajapati、Vishal B. Purohit、Luis Andre Baptista、Jemin R. Avalani、Nirav H. Sapariya、Sharad C. Karad、Dipak K. Raval

  DOI：10.1016/j.tet.2023.133783

  日期：2024.1