1-(2-fluorophenyl)-3-(2-methoxyphenyl)prop-2-yn-1-one | 1593267-92-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-fluorophenyl)-3-(2-methoxyphenyl)prop-2-yn-1-one
• CAS: 1593267-92-5
• 化学式: C₁₆H₁₁FO₂
• 分子量: 254.261
• InChiKey: RIIHHIASIOAQBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-fluorophenyl)-3-(2-methoxyphenyl)prop-2-yn-1-one 在 一水合肼 作用下， 以 乙腈 为溶剂， 生成 5-(2-fluorophenyl)-3-(2-methoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

  摘要：

  Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.

  DOI：

  10.1021/acschembio.5b00934
• 作为产物：
  描述：

  2-乙炔基苯甲醚 、 邻氟苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2-fluorophenyl)-3-(2-methoxyphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

  摘要：

  Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.

  DOI：

  10.1021/acschembio.5b00934

文献信息

• Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
  作者：Karoline T. Neumann、Simon R. Laursen、Anders T. Lindhardt、Benny Bang-Andersen、Troels Skrydstrup

  DOI：10.1021/ol5007289

  日期：2014.4.18

  A general procedure for the palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides is reported, using near stoichiometric amounts of carbon monoxide. The method allows a broad substrate scope in moderate to excellent yields. The formed alkynone motive serves as a platform for synthesis of various heterocyclic structures, including pyrimidines. Furthermore, the presented strategy allows

  据报道，使用接近化学计量的一氧化碳，钯催化芳基溴化物的羰基化Sonogashira偶联反应的一般程序。该方法允许以中等至优异的产率在宽范围的基材上使用。形成的炔酮动机用作合成各种杂环结构（包括嘧啶）的平台。此外，提出的策略允许有效的13 C标记。
• Correction to Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
  作者：Karoline T. Neumann、Simon R. Laursen、Anders T. Lindhardt、Benny Bang-Andersen、Troels Skrydstrup

  DOI：10.1021/acs.orglett.5b01250

  日期：2015.5.15

  Solvent peaks and in some cases minor impurities had been removed from the 1H and 13C NMR spectra reported for compounds 3, 5, 7, 9, 10, 12, 15, 18b, 23, 26b, 27, 29, 30b, and 31b. Original FIDs were located for compounds 3, 7, 9, 12, 15, 29, 30b, and 31b, and the spectra were reprocessed and have been replaced in the revised Supporting Information. For compounds 10, 18b, 23, and 26b, the reactions

  溶剂峰和在某些情况下少量杂质已经从除去1 H和13 C NMR谱报告为化合物3，5，7，9，10，12，15，18B，23，26B，27，29，30B，和31b。原始的FID分别位于对化合物3，7，9，12，15，29，30b的和31b，对光谱进行了重新处理，并在修订的《支持信息》中进行了替换。对于化合物10，图18b，23，和26B中，反应重新运行并已提供的新的光谱在校正的支持信息。对于化合物5，原始支持信息中提交了错误的光谱。现在，正确的光谱已包含在修订的《支持信息》中。对于化合物27，未找到原始FID，而是获得了新光谱，并在修订的《支持信息》中提供了这些光谱。光谱编辑不会影响已发表论文的任何结论。根据修订后的光谱校正的产率如下：10（产率87％），18b（产率98％），23（产率90％）和26b（产率95％）。包含修改后的光谱的文件。可在ACS出版物网站上免费获得支持信息，网址为：DOI：10