4-Methyl-7-[(4-methyl-2-oxochromen-7-yl)disulfanyl]chromen-2-one | 1141172-43-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-Methyl-7-[(4-methyl-2-oxochromen-7-yl)disulfanyl]chromen-2-one
• CAS: 1141172-43-1
• 化学式: C₂₀H₁₄O₄S₂
• 分子量: 382.461
• InChiKey: OOSJONRUFLIDKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Methyl-7-[(4-methyl-2-oxochromen-7-yl)disulfanyl]chromen-2-one 、 乙酰溴代纤维二糖 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以86%的产率得到(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(2R,3R,4S,5R,6S)-4,5-diacetoxy-2-(acetoxymethyl)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)thio]tetrahydro-2H-pyran-3-yl]oxy}tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

  摘要：

  A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.

  DOI：

  10.1016/j.carres.2014.07.011
• 作为产物：
  描述：

  7-疏基-4-甲基香豆素 在 aluminum oxide 、 potassium permanganate 作用下， 反应 0.17h， 以28%的产率得到4-Methyl-7-[(4-methyl-2-oxochromen-7-yl)disulfanyl]chromen-2-one
  参考文献：
  名称：

  7-Mercapto-4-methylcoumarin as a reporter of thiol binding to the CdSe quantum dot surface

  摘要：

  7-巯基-4-甲基香豆素与核壳CdSe-ZnS量子点表面的相互作用会产生特征吸收和发射带，这是硫醇在纳米粒子表面相互作用的极佳报告。

  DOI：

  10.1039/b900606k

文献信息

• Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite
  作者：Cheerladinne Venkateswarlu、Vibha Gautam、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2014.07.011

  日期：2014.9

  A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.
• 7-Mercapto-4-methylcoumarin as a reporter of thiol binding to the CdSe quantum dot surface
  作者：María González-Béjar、Mathieu Frenette、Larissa Jorge、J. C. Scaiano

  DOI：10.1039/b900606k

  日期：——

  Interaction of 7-mercapto-4-methylcoumarin with the surface of core–shell CdSe–ZnS quantum dots leads to characteristic absorption and emission bands that are excellent reporters for thiol interactions at the nanoparticle surface.

  7-巯基-4-甲基香豆素与核壳CdSe-ZnS量子点表面的相互作用会产生特征吸收和发射带，这是硫醇在纳米粒子表面相互作用的极佳报告。