2-(2-Chloro-phenyl)-5-phenyl-2,4-dihydro-pyrazol-3-one | 87277-68-7

• 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-(2-Chloro-phenyl)-5-phenyl-2,4-dihydro-pyrazol-3-one
• 英文别名: 2-(2-chlorophenyl)-5-phenyl-4H-pyrazol-3-one
• CAS: 87277-68-7
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: KKGCNWWFWKTLHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Chloro-phenyl)-5-phenyl-2,4-dihydro-pyrazol-3-one 在 三乙胺 作用下， 反应 38.0h， 生成 1-(2-Chloro-phenyl)-4,6,6-trimethyl-3-phenyl-1,6-dihydro-pyrano[2,3-c]pyrazole
  参考文献：
  名称：

  A New and Convenient Method for the Synthesis of 1,3-Disubstituted 4,6,6-Trimethyl-1, 6-dihydropyrano[2,3-c]pyrazoles

  摘要：

  DOI：

  10.1055/s-1983-30393
• 作为产物：
  描述：

  2-氯苯肼盐酸盐 、 苯甲酰乙酸乙酯 在 碳酸氢钠 、 溶剂黄146 作用下， 反应 1.5h， 生成 2-(2-Chloro-phenyl)-5-phenyl-2,4-dihydro-pyrazol-3-one
  参考文献：
  名称：

  The structure-based optimization of δ-sultone-fused pyrazoles as selective BuChE inhibitors

  摘要：

  Structure-based optimization was conducted to improve the potency and selectivity of BuChE inhibitors with delta-sulfonolactone-fused pyrazole scaffold. By mimicking the hydrophobic interactions of donepezil at PAS, the introduction of a tertiary benzylamine at 5-position can significantly increase BuChE inhibitory activity. Compounds C4 and C6 were identified as high selective nanomolar BuChE inhibitors (IC50 = 8.3 and 7.7 nM, respectively), which exhibited mild antioxidant capacity, nontoxicity, lipophilicity and neuroprotective activity. Kinetic studies showed that BuChE inhibition of compound C6 was mixed-type against BuChE (K-i = 24 nM) and >2000-fold selectivity for BuChE over AChE. The proposed binding mode of new inhibitors was consistent with the results of structure-activity relationship analysis. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112273

文献信息

• Asymmetric [3 + 3] Annulation of Copper–Allenylidenes with Pyrazolones: Synthesis of Chiral 1,4-Dihydropyrano[2,3-<i>c</i>]pyrazoles
  作者：Feng Jiang、Xinping Feng、Rou Wang、Xing Gao、Hao Jia、Yumei Xiao、Cheng Zhang、Hongchao Guo

  DOI：10.1021/acs.orglett.8b02214

  日期：2018.9.7

  The copper-catalyzed asymmetric [3 + 3] annulation of ethynyl benzoxazinanones with pyrazolones has been achieved, providing simple access to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in moderate to excellent yields with excellent enantioselectivities (up to 99% ee). Compared with previous annulation reactions of copper–allenylidenes from ethynyl benzoxazinanones, the current reaction fused the

  乙炔基苯并恶嗪酮与吡唑啉酮的铜催化不对称环化[3 + 3]已实现，可轻松获得1,4-二氢吡喃并[2,3- c ]吡唑衍生物，且产率中等至优异，对映选择性极佳（高达99 ％ee）。与以前的乙炔基苯并恶嗪酮的铜-亚烯基环化反应相比，当前反应将炔丙基部分的三个碳原子融合成杂环骨架。
• Design, synthesis of new magenta dyestuffs based on thiazole azomethine disperse reactive dyes with antibacterial potential on both dyes and gamma-irradiated dyed fabric
  作者：Seham A. Ibrahim、Hala F. Rizk、Dina S. Aboul-Magd、Ahmed Ragab

  DOI：10.1016/j.dyepig.2021.109504

  日期：2021.9

  high ultraviolet protection. The advantage of synthesizing these dyes is quite facile, and scale-up is feasible, preferring industrial dyeing applications. The designed thiazole azomethine dyes exhibited broad-spectrum antibacterial agents against MDR Gram-positive and Gram-negative bacterial isolates, which will facilitate their rational usage in multiple therapeutic applications. Our findings also demonstrate

  合成了一系列新型洋红色偶氮甲碱活性分散染料并应用于涤棉混纺织物。各种光谱和分析技术表征了所有合成的染料。所有合成分子的所得数据和理论值与所提出的分子结构非常吻合。这些染料已证明它们在染色混纺织物方面的效率，因为它们在牢度特性、比色数据和吸尽、固色研究方面都取得了令人满意的结果。此外，染色织物进行了紫外线防护系数测试，并提供了高紫外线防护。合成这些染料的优点是非常容易，并且规模化是可行的，更适合工业染色应用。设计的噻唑偶氮甲碱染料对 MDR 革兰氏阳性和革兰氏阴性细菌分离株具有广谱抗菌作用，这将有助于它们在多种治疗应用中的合理使用。我们的研究结果还证明了使用伽马辐射对染色织物进行消毒的可能性以及辐射增强其抗菌活性的能力，从而抑制纺织品表面的任何细菌生长。分子对接研究表明，染料与 DNA 促旋酶的活性位点 (2XCT) 之间具有良好的结合作为首选模式。我们的研究结果还证明了使用伽马辐射对染色织
• Organocatalytic diastereo- and enantioselective conjugate addition of pyrazol-3-ones to 3-trifluoroethylidene oxindoles with a newly developed squaramide catalyst
  作者：Zhao Han、Jiaping Jin、Alemayehu Gashaw Woldegiorgis、Xufeng Lin

  DOI：10.1039/d2ra05088a

  日期：——

  An efficient organocatalytic conjugated addition reaction of pyrazol-3-ones with 3-trifluoroethylidene oxindoles has been developed for the synthesis of enantioenriched triflouromethylated indolin-2-ones bearing adjacent tertiary chiral centers in good yields and good to excellent diastereo- and enantioselectivities. The use of a newly developed chiral spirobiindane-derived squaramide catalyst is essential

  吡唑-3-酮与3-三氟亚乙基羟吲哚的高效有机催化共轭加成反应已被开发用于以良好的收率和良好的非对映选择性和对映选择性合成具有相邻叔手性中心的对映富集的三氟甲基化二氢吲哚-2-酮。使用新开发的手性螺二茚衍生方酰胺催化剂对于实现高非对映和对映选择性至关重要。
• 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。
• Novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethane derivatives using formamide or N-methylformamide
  作者：Fung Fuh Wong、Yu-Ying Huang

  DOI：10.1016/j.tet.2011.03.089

  日期：2011.5

  A novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethanes was developed by reacting pyrazolones with formamide or N-methylformamide in the presence of phosphorous oxychloride POCl3 coupling agent. This method can efficiently provide a series of dipyrazolylmethane derivatives as the main products in excellent yields without the formylated products. Our experimental result was different with the classical Vilsmeier-type reaction. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.