1-(2-methyl-6-(p-methylphenyl)pyridin-3-yl)ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(2-methyl-6-(p-methylphenyl)pyridin-3-yl)ethanone
• 英文别名: 3-acetyl-2-methyl-6-(p-methyphenyl)pyridine；1-(2-methyl-6-(p-tolyl)pyridin-3-yl)ethan-1-one；1-(2-methyl-6-p-tolyl-[3]pyridyl)-ethanone；1-(2-Methyl-6-p-tolyl-[3]pyridyl)-aethanon；1-(2-Methyl-6-p-tolylpyridin-3-yl)ethanone；1-[2-methyl-6-(4-methylphenyl)pyridin-3-yl]ethanone
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: FDHWJLUZVRMCBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-6-(p-methylphenyl)pyridin-3-yl)ethanone 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1,1-dimethyl-3-(4-(2-methyl-6-p-tolylpyridin-3-yl)pyrimidin-2-yl)guanidine
  参考文献：
  名称：

  新型嘧啶衍生物作为潜在抗菌剂的合成与分子对接研究。

  摘要：

  摘要 本工作描述了一些新型嘧啶衍生物的体外抗菌评价。设计，合成并初步探索了22种目标化合物的抗菌活性。抗菌测定表明，某些目标化合物对细菌和真菌（包括耐药病原体）表现出明显的抑制作用。化合物7c对革兰氏阳性细菌（例如金黄色葡萄球菌4220），革兰氏阴性细菌（例如大肠杆菌1924）和真菌白色念珠菌7535表现出最强的抑制活性，MIC为2.4μmol/ L。化合物7c也是最有效的，对四种具有多重耐药性的革兰氏阳性细菌菌株的MIC为2.4或4.8μmol/ L。在人正常肝细胞（L02细胞）中评估了化合物7c，10a，19d和26b的毒性评估。分子对接模拟和分析表明，化合物7c与二氢叶酸还原酶（DHFR）的活性腔具有良好的相互作用。体外酶研究暗示化合物7c也显示出DHFR抑制作用。 图形摘要

  DOI：

  10.1007/s11030-019-10019-8
• 作为产物：
  描述：

  4-氨基-3-戊烯-2-酮 、 3-oxo-3-p-tolyl-propionaldehyde 在 乙醚 作用下， 生成 1-(2-methyl-6-(p-methylphenyl)pyridin-3-yl)ethanone
  参考文献：
  名称：

  Basu; Banerjee, Journal of the Indian Chemical Society, 1935, vol. 12, p. 665,668

  摘要：

  DOI：

文献信息

• Microwave-assisted regioselective one-pot synthesis of trisubstituted pyridine scaffolds using K₅CoW₁₂O₄₀.3H₂O under solvent free conditions
  作者：Srinivas Kantevari、Mahankhali Venu Chary、Srinivasu V. N. Vuppalapati、N. Lingaiah

  DOI：10.1002/jhet.5570450424

  日期：2008.7

  A highly efficient, microwave-assisted, regioselective synthesis of 2,3-disubstituted-6-arylpyridines and new series of 7,7-dimethyl-2-aryl-5,6,7,8-tetrahydroquinoline-5-ones from enaminones in the presence of K5CoW12O40.3H2O (1.0 mol %) as heterogeneous catalyst under solvent free conditions is reported.

  高效的微波辅助区域选择性合成的2,3-二取代的6-芳基吡啶和新的7,7-二甲基2-芳基5,6,7,8-四氢喹啉5-酮从氨基酮中合成。据报道在无溶剂条件下存在K 5 CoW 12 O 40 .3H 2 O（1.0 mol％）作为非均相催化剂。
• Robust and General Late-Stage Methylation of Aryl Chlorides: Application to Isotopic Labeling of Drug-like Scaffolds
  作者：Elliot Davenport、Daniela E. Negru、Geoff Badman、David M. Lindsay、William J. Kerr

  DOI：10.1021/acscatal.3c02761

  日期：2023.9.1

  highly efficient, robust palladium-catalyzed approach, optimized via high-throughput experimentation, for the methylation of aryl chlorides using potassium methyltrifluoroborate. A practically straightforward route to isotopically labeled methylating agents has also been developed, and the methodology applied to isotopologue synthesis, including the installation of isotopic labels in a range of drug-like

  用于药物发现和开发的同位素标记化合物的制备提出了独特的挑战。必须使用珍贵且通常昂贵的同位素富集试剂，将稳定同位素和放射性同位素尽可能有效地整合到复杂的生物活性分子中。由于药物分子中甲基的普遍存在和重要性，需要进行通用的后期甲基化，以允许碳同位素和氢同位素的掺入。在此，我们报告了一种高效、稳健的钯催化方法，通过高通量实验进行优化，用于使用甲基三氟硼酸钾对芳基氯进行甲基化。还开发了一种实际上直接的同位素标记甲基化剂途径，并将该方法应用于同位素体合成，包括在一系列药物样支架中安装同位素标记。
• Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines
  作者：Huanfeng Jiang、Jidan Yang、Xiaodong Tang、Jianxiao Li、Wanqing Wu

  DOI：10.1021/acs.joc.5b01621

  日期：2015.9.4

  A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.
• A highly efficient regioselective one-pot synthesis of 2,3,6-trisubstituted pyridines and 2,7,7-trisubstituted tetrahydroquinolin-5-ones using K5CoW12O40·3H2O as a heterogeneous recyclable catalyst
  作者：Srinivas Kantevari、Mahankhali Venu Chary、Srinivasu V.N. Vuppalapati

  DOI：10.1016/j.tet.2007.10.014

  日期：2007.12

  A systematic investigation into the regioselective one-pot, three-component condensation of enaminones la-g, beta-dicarbonyl compounds 2a-c, and ammonium acetate in the presence of a catalytic amount of K5CoW12O40 center dot 3H(2)O (0.01 equiv or 1.0 mol %) under solvent free conditions, as well as in refluxing isopropanol, has been reported. The reaction was highly efficient to produce 2,3,6-trisubstituted pyridines 3a-g, 4a-g, and novel 2,7,7-trisubstituted-5,6,7,8-tetrahydroquinoline-5-ones 5a-g in excellent yields. The present procedure offers advantages of short reaction time, simple work-up, and the catalyst exhibited remarkable reusable activity. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and molecular docking studies of novel pyrimidine derivatives as potential antibacterial agents
  作者：Xue-Qian Bai、Chun-Shi Li、Ming-Yue Cui、Ze-Wen Song、Xing-Yu Zhou、Chao Zhang、Yang Zhao、Tian-Yi Zhang、Tie-Yan Jiang

  DOI：10.1007/s11030-019-10019-8

  日期：2020.11

  Abstract The present work describes the in vitro antibacterial evaluation of some new pyrimidine derivatives. Twenty-two target compounds were designed, synthesized and preliminarily explored for their antimicrobial activities. The antimicrobial assay revealed that some target compounds exhibited significantly inhibitory efficiencies toward bacteria and fungal including drug-resistant pathogens. Compound

  摘要 本工作描述了一些新型嘧啶衍生物的体外抗菌评价。设计，合成并初步探索了22种目标化合物的抗菌活性。抗菌测定表明，某些目标化合物对细菌和真菌（包括耐药病原体）表现出明显的抑制作用。化合物7c对革兰氏阳性细菌（例如金黄色葡萄球菌4220），革兰氏阴性细菌（例如大肠杆菌1924）和真菌白色念珠菌7535表现出最强的抑制活性，MIC为2.4μmol/ L。化合物7c也是最有效的，对四种具有多重耐药性的革兰氏阳性细菌菌株的MIC为2.4或4.8μmol/ L。在人正常肝细胞（L02细胞）中评估了化合物7c，10a，19d和26b的毒性评估。分子对接模拟和分析表明，化合物7c与二氢叶酸还原酶（DHFR）的活性腔具有良好的相互作用。体外酶研究暗示化合物7c也显示出DHFR抑制作用。 图形摘要