2-(4-bromophenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one | 14580-15-5

• 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-bromophenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 1-(4-bromophenyl)-3-methyl-1H-pyrazol-5(4H)-one；2-(4-Bromo-phenyl)-5-methyl-2,4-dihydro-pyrazol-3-one；1-(4-bromophenyl)-3-methyl-4,5-dihydro-1H-pyrazol-5-one；2-(4-bromophenyl)-5-methyl-4H-pyrazol-3-one
• CAS: 14580-15-5
• 化学式: C₁₀H₉BrN₂O
• mdl: MFCD00466111
• 分子量: 253.098
• InChiKey: DFQPWWDYYNSRQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one 生成 1,2-二氢-2-(4-溴苯基)-1,5-二甲基-3H-吡唑-3-酮
  参考文献：
  名称：

  .beta.-lactam antibacterial agents and compositions containing them

  摘要：

  式（1）的化合物或其药学上可接受的盐或体内水解酯： 其中，R1为苯基，取代苯基或含有最多三个氧、硫或氮的5-或6元杂环环，可选地取代羟基、氨基、卤素或C1-6烷氧基; X代表; 其中，RY为甲基或乙酰基; R2和R3可以相同也可以不同，每个都是氢、芳基、杂环基或可选地由芳基或杂环基取代的C1-6烷基; R4为氢、C1-6烷基羰基基、芳基、杂环基、可选地由芳基或杂环基取代的C1-6烷基; R5代表氢、甲氧基或-NHCHO; Y为: 其中，Y1为氧、硫或-CH2-，Z代表氢、卤素或有机基，例如C1-4烷氧基，-CH2Q或-CH=CH-Q，其中Q代表氢、卤素、羟基、巯基、氰基、羧基、羧酸酯、C1-4烷氧基、酰氧基、芳基、通过碳键结合的杂环基、杂环硫基或通过氮键结合的含氮杂环基。

  公开号：

  US04537886A1
• 作为产物：
  描述：

  4-溴苯肼盐酸盐 在 ammonium hydroxide 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-(4-bromophenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  Design, synthesis and photophysical properties of A-D-A-D-A small molecules for photovoltaic application

  摘要：

  A series of linear-conjugated small molecule compounds featured with the acceptor-donor-acceptor-donor-acceptor (A-D-A-D-A) structure were designed, synthesized and characterized. The films of the compounds showed a broad UV-Vis absorption range of 300-800 nm with high molar absorption coefficient of more than 1.0 x 10(4) cm(-1). Their hole-mobility can be as high as 1.0 x 10(-3) cm(2) V-1 s(-1). The compounds have a compatible HOMO energy level of -5.0 eV to PC71BM and a high solubility up to 20 mg mL(-1) in chloroform. Therefore, compounds can blend with PC71BM in the chloroform and form an active layer for a photovoltaic cell device by spin-coating of the blend solution. A maximum power conversion efficiency of 3.2% was achieved with the DERH3TT solar cell device. These results indicate that the A-D-A-D-A small molecules with electron-withdrawing dyes as terminals are promising candidates for the high efficiency solution processed organic photovoltaic cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.009

文献信息

• Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole‐4,5‐Diones and Indoline‐2,3‐Diones
  作者：Rong‐Hui Wang、Ya‐Ling Li、Hong‐Jiao He、You‐Cai Xiao、Fen‐Er Chen

  DOI：10.1002/chem.202005081

  日期：2021.3

  The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin‐4,5‐diones and isatins have been developed. In the presence of morpholine‐containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes

  已经开发了对环二酮（包括吡唑啉-4,5-二酮和靛红）的催化对映选择性二有机锌。在含有吗啉的手性氨基醇配体存在的情况下，相应的手性环状叔醇以良好至极佳的收率（高达97％）和对映选择性（高达95％ee）生产。该方案的显着特征包括温和的反应条件，无路易斯酸添加剂和宽泛的官能团耐受性。
• 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。
• The selective condensation of pyrazolones to isatins in aqueous medium
  作者：Yong Zhang、Long-Jun Nie、Liang Luo、Jia-Xin Mao、Jin-Xiang Liu、Guo-Hai Xu、Deliang Chen、Hai-Qing Luo

  DOI：10.1016/j.tet.2019.130916

  日期：2020.2

  The selective condensation of pyrazolones with isatins using water as the reaction medium is presented. This strategy provides an environmentally benign synthetic route to synthesize various potentially bioactive pyrazolone substituted oxindoles.

  提出了以水为反应介质的吡唑啉酮与靛红的选择性缩合反应。该策略提供了一种环境友好的合成途径，可以合成各种可能具有生物活性的吡唑啉酮取代的羟吲哚。
• Regioselective N-Addition/Substitution Reaction of α-Alkylidene Pyrazolinones with Propargyl Sulfonium Salts to Construct Allylthio-Containing Pyrazolones
  作者：Shou-Jie Shen、Xiao-Li Du、Xiao-Li Xu、Ming-Gang Zhao、Jin-Yan Liang

  DOI：10.1021/acs.joc.9b02029

  日期：2019.10.4

  The regioselective N-addition/substitution reaction between α-alkylidene pyrazolinones and propargyl sulfonium salts has been developed to construct functionalized allylthio-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones act as N-nucleophilic agents which are distinguished from reported C-nucleophilic reactions. Excellent regioselectivity, readily available starting

  已经开发了α-亚烷基吡唑啉酮类与炔丙基salts盐之间的区域选择性N-加成/取代反应，以中等至优异的产率构建官能化的含烯丙基硫基的吡唑啉酮。α-亚烷基吡唑啉酮类作为N-亲核试剂，与已报道的C-亲核反应不同。出色的区域选择性，易于获得的起始原料，广泛的底物范围，克级合成以及简单的操作，说明了这种新反应途径的合成优势。
• Structure-activity relationships of pyrazole-4-carbodithioates as antibacterials against methicillin–resistant Staphylococcus aureus
  作者：Hiwa Majed、Tatiana Johnston、Celine Kelso、Enrico Monachino、Slobodan Jergic、Nicholas E. Dixon、Eleftherios Mylonakis、Michael J. Kelso

  DOI：10.1016/j.bmcl.2018.09.038

  日期：2018.12

  synthesized, their anti-MRSA structure-activity relationships evaluated and selectivity versus human HKC-8 cells determined. Minimum inhibitory concentrations (MIC) ranged from 0.5 to 64 μg/mL and up to 16-fold selectivity was achieved. The 4-carbodithioate function was found to be essential for activity but non-specific reactivity was ruled out as a contributor to antibacterial action. The study supports

  耐甲氧西林的金黄色葡萄球菌（MRSA）是严重的医院获得性感染的主要原因，并且对居民护理设施中的高发病率和高死亡率负责。需要新的抗MRSA药物来对抗目前对抗生素的耐药性上升。我们最近报道了5-羟基-3-甲基-1-苯基-1 H-吡唑-4-碳二硫代酸酯（HMPC）作为一种针对MRSA的新型抑菌剂，似乎通过一种新机制起作用。在这里，合成了HMPC的29个类似物，评估了它们的抗MRSA结构-活性关系，并确定了相对于人HKC-8细胞的选择性。最小抑菌浓度（MIC）为0.5至64μg/ mL，选择性达到16倍。发现4-碳二硫代硫酸盐功能对于活性是必不可少的，但是排除了非特异性反应性作为抗菌作用的贡献者。该研究支持旨在阐明这种有趣的新型抗MRSA药物分子靶标的进一步工作。

表征谱图