1-(6-methoxynaphthalen-2-yl)-2-phenylethane-1,2-dione | 340232-52-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(6-methoxynaphthalen-2-yl)-2-phenylethane-1,2-dione
• 英文别名: 1-(6-Methoxynaphthalen-2-yl)-2-phenylethane-1,2-dione
• CAS: 340232-52-2
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: LYVCWTYZZBQYES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-methoxynaphthalen-2-yl)-2-phenylethane-1,2-dione 、 特戊醛 在 ammonium acetate 作用下， 以 正丁醇 为溶剂， 反应 5.0h， 以52 mg的产率得到2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-5-phenyl-1H-imidazole
  参考文献：
  名称：

  Trisubstituted Imidazoles as Mycobacterium tuberculosis Glutamine Synthetase Inhibitors

  摘要：

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.

  DOI：

  10.1021/jm201212h
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium permanganate 、 copper(l) iodide 、 氧气 作用下， 以 二乙胺 、 丙酮 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(6-methoxynaphthalen-2-yl)-2-phenylethane-1,2-dione
  参考文献：
  名称：

  Trisubstituted Imidazoles as Mycobacterium tuberculosis Glutamine Synthetase Inhibitors

  摘要：

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.

  DOI：

  10.1021/jm201212h

文献信息

• Mild Mn(OAc)₃-Mediated Aerobic Oxidative Decarboxylative Coupling of Arylboronic Acids and Arylpropiolic Acids: Direct Access to Diaryl 1,2-Diketones
  作者：Wen-Xin Lv、Yao-Fu Zeng、Shang-Shi Zhang、Qingjiang Li、Honggen Wang

  DOI：10.1021/acs.orglett.5b01265

  日期：2015.6.19

  A simple and efficient method for the synthesis of diaryl 1,2-diketones has been developed. The reaction represents the first example of diaryl 1,2-diketones that are synthesized directly from arylboronic acids and arylpropiolic acids by a radical pathway in moderate to good yields. This reaction proceeds under mild reaction conditions and with good tolerance of a variety of functional groups. Preliminary

  已经开发了一种简单有效的合成二芳基1,2-二酮的方法。该反应代表二芳基1,2-二酮的第一个实例，该二芳基1,2-二酮是通过自由基途径由芳基硼酸和芳基丙酸直接合成的，产率中等至良好。该反应在温和的反应条件下进行，并且对各种官能团具有良好的耐受性。进行了初步的力学研究。
• Oxidation of alkynes using PdCl2/CuCl2 in PEG as a recyclable catalytic system: one-pot synthesis of quinoxalines
  作者：S. Chandrasekhar、N. Kesava Reddy、V. Praveen Kumar

  DOI：10.1016/j.tetlet.2010.05.006

  日期：2010.7

  Alkynes were oxidized efficiently using the catalytic amount of PdCl2 and CuCl2 in PEG-400 in the presence of water, providing excellent yields of the corresponding 1,2-diketones. A variety of alkynes were well-suited substrates for the oxidation under the described conditions. Further, the optimized conditions were successfully utilized for the one-pot synthesis of 2,3-disubstituted quinoxaline derivatives

  在水存在下，使用PEG-400中的催化量的PdCl 2和CuCl 2催化有效地氧化炔烃，从而提供了极佳的相应1,2-二酮收率。多种炔烃是在所述条件下用于氧化的非常合适的底物。此外，优化的条件已成功用于一锅合成2，3-二取代的喹喔啉衍生物。
• Trisubstituted Imidazoles as <i>Mycobacterium tuberculosis</i> Glutamine Synthetase Inhibitors
  作者：Johan Gising、Mikael T. Nilsson、Luke R. Odell、Samir Yahiaoui、Martin Lindh、Harini Iyer、Achyut M. Sinha、Bachally R. Srinivasa、Mats Larhed、Sherry L. Mowbray、Anders Karlén

  DOI：10.1021/jm201212h

  日期：2012.3.22

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.