3-methyl-2-methylsulfanylchromen-4-one | 868732-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-methyl-2-methylsulfanylchromen-4-one
• 英文别名: 3-methyl-2-(methylthio)-4H-chromen-4-one；3-Methyl-2-methylsulfanyl-chromen-4-one
• CAS: 868732-17-6
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: OUHNLCKHNFXCAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  307.0±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-2-methylsulfanylchromen-4-one 在 Raney nickel 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以81%的产率得到甲色酮
  参考文献：
  名称：

  碘介导的 2-(甲硫基)-4 H -chromen-4-ones 的合成及其卤化反应研究

  摘要：

  开发了一种有效的碘介导方法，用于通过容易获得的 1-(2-苄氧基-芳基)-3,3-双-甲基硫烷基的分子内环化合成功能化的 2-(甲硫基)-4 H-色烯-4-酮-丙烯酮。合成的 chromen-4-ones 是各种化学反应的关键前体。从机制上讲，我们观察到碘介导的二硫代乙缩醛分子内环化是通过自由基途径进行的。3-Halo-2-(methylthio)-4 H -chromen-4-ones 是通过各种两锅或一锅卤化方法实现的。

  DOI：

  10.1021/acs.joc.1c00788
• 作为产物：
  描述：

  2'-羟基苯丙酮 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 116.0h， 生成 3-methyl-2-methylsulfanylchromen-4-one
  参考文献：
  名称：

  The design and synthesis of novel inhibitors of NADH:ubiquinone oxidoreductase

  摘要：

  Potent new inhibitors of NADH:ubiquinone oxidoreductase (complex 1) have been designed, with the help of molecular modelling, by hybridisation of known complex I inhibitors with inhibitors of cytochrome c oxidoreductase. The most interesting compound was the chromone 7 which was a selective inhibitor of complex I (IC50 15 nM) and showed acaricidal activity against spider mites. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.022

文献信息

• Contrast agents for myocardial perfusion imaging
  申请人：Radeke S. Heike

  公开号：US20050244332A1

  公开（公告）日：2005-11-03

  The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.

  本公开涉及部分用于心肌灌注成像的化合物和方法，包括向患者注射一种对MC-1结合的化合物和成像基团构成的造影剂，并利用诊断成像对患者进行扫描。
• CONTRAST AGENTS FOR MYOCARDIAL PERFUSION IMAGING
  申请人：Radeke Heike S.

  公开号：US20090104118A1

  公开（公告）日：2009-04-23

  The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.

  本公开涉及部分化合物和成像心肌灌注的方法，包括向患者注射一种对MC-1具有结合作用的化合物和成像基团构成的对比剂，并使用诊断成像对患者进行扫描。
• Synthesis and Biological Evaluation of the Mitochondrial Complex 1 Inhibitor 2-[4-(4-Fluorobutyl)benzylsulfanyl]-3-methylchromene-4-one as a Potential Cardiac Positron Emission Tomography Tracer
  作者：Heike Radeke、Kelley Hanson、Padmaja Yalamanchili、Megan Hayes、Zhi-Qin Zhang、Michael Azure、Ming Yu、Mary Guaraldi、Mikhail Kagan、Simon Robinson、David Casebier

  DOI：10.1021/jm0701831

  日期：2007.9.1

  A series of fluorinated chromone analogs with IC50 values ranging from 9 to 133 nM for the mitochondrial complex I (MC-I) has been prepared. A structure -activity relationship (SAR) study of the most potent fluorinated chromone analog 10 demonstrated the linkage heteroatom preference of the side chain region of the molecule while maintaining potent MC-I inhibitory activity. Tissue distribution studies 30 min after [F-18]10 administration to Sprague-Dawley (SD) rats demonstrated high uptake of the radiotracer from the blood pool into the myocardium (2.24% ID/g), kidney (1.93% ID/g), and liver (2.00% ID/g). After 2 h about 66% of the activity in the myocardiurn at 30 min had been retained, whereas -70% had been cleared from the liver and kidney. MicroPET images of SD rats after [F-18]10 administration allowed easy assessment of the myocardium through 60 min with minimal lung or liver interference.
• Synthesis of functionalized flavones from 3-halo-2-(methylthio)-4H-chromen-4-ones
  作者：Amr Elagamy、Laila K. Elghoneimy、Reem K. Arafa、Ramendra Pratap

  DOI：10.1016/j.tetlet.2022.153882

  日期：2022.6

  A simple and efficient method for the synthesis of flavones was achieved by selective sulfide Liebeskind-Srogl cross-coupling reaction of 2-(methylthio)-4H-chromen-4-ones and 3-halo-2-(methylthio)-4H-chromen-4-ones with arylboronic acids. This method is the first example of employing Liebeskind-Srogl coupling for the synthesis of flavones. Various aryl groups can be directly installed to the chromone
• EP1740225A4
  申请人：——

  公开号：EP1740225A4

  公开（公告）日：2009-08-19