[2-(4-Methylphenyl)-4-oxochromen-3-yl] 4-methylbenzenesulfonate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: [2-(4-Methylphenyl)-4-oxochromen-3-yl] 4-methylbenzenesulfonate
• 化学式: C₂₃H₁₈O₅S
• 分子量: 406.459
• InChiKey: SFEGGNBCHVXXQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(4-Methylphenyl)-4-oxochromen-3-yl] 4-methylbenzenesulfonate 、 甲胺 以 四氢呋喃 为溶剂， 反应 24.0h， 以93%的产率得到(E)-2-[1-methylamino-1-(4-methylphenyl)methylidene]benzofuran-3-one
  参考文献：
  名称：

  The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines

  摘要：

  A rearrangement of 3-tosylflavone to the corresponding 1'-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1'-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.062
• 作为产物：
  描述：

  1-(2-羟基苯基)-3-(4-甲基苯基)-2-丙烯-1-酮 在 双氧水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 [2-(4-Methylphenyl)-4-oxochromen-3-yl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines

  摘要：

  A rearrangement of 3-tosylflavone to the corresponding 1'-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1'-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.062

文献信息

• The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines
  作者：Wolfgang Kandioller、Mario Kubanik、Anna K. Bytzek、Michael A. Jakupec、Alexander Roller、Bernhard K. Keppler、Christian G. Hartinger

  DOI：10.1016/j.tet.2015.09.062

  日期：2015.11

  A rearrangement of 3-tosylflavone to the corresponding 1'-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1'-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed. (C) 2015 Elsevier Ltd. All rights reserved.