5-methoxy-2-phenyl trifluoromethanesulfonate | 957049-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methoxy-2-phenyl trifluoromethanesulfonate
• 英文别名: Ethyl 2-[4-methoxy-2-(trifluoromethylsulfonyloxy)phenyl]-2-oxoacetate
• CAS: 957049-46-6
• 化学式: C₁₂H₁₁F₃O₇S
• 分子量: 356.276
• InChiKey: ACGAKYJYXNHZTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-phenyl trifluoromethanesulfonate 、 3-氟苯基硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 生成 2-[2-(3-Fluorophenyl)-4-methoxyphenyl]-2-oxoacetic acid
  参考文献：
  名称：

  An Efficient and Scalable Synthesis of Substituted Phenanthrenequinones by Intramolecular Friedel−Crafts Reaction of Imidazolides

  摘要：

  An efficient synthesis of 9,10-phenanthrenequinones is described. The two carbonyl groups were introduced by an orthoselective intermolecular Friedel-Crafts reaction of 3-methoxyphenol with ethyl chlorooxoacetate. The formation of a biaryl bond by Suzuki-Miyaura coupling reaction, followed by the hydrolysis of the ester, gave a biaryloxoacetic acid. Treatment of this acid with CDI gave the corresponding imidazolide. The ring closure to the desired phenanthrenequinone was accomplished by intramolecular Friedel-Crafts reaction of the imidazolide promoted by TiCl4.

  DOI：

  10.1021/ol071261h
• 作为产物：
  描述：

  三氟甲磺酸酐 、 ethyl 2-(4-methoxy-2-hydroxyphenyl)-2-oxoethanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-methoxy-2-phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  An Efficient and Scalable Synthesis of Substituted Phenanthrenequinones by Intramolecular Friedel−Crafts Reaction of Imidazolides

  摘要：

  An efficient synthesis of 9,10-phenanthrenequinones is described. The two carbonyl groups were introduced by an orthoselective intermolecular Friedel-Crafts reaction of 3-methoxyphenol with ethyl chlorooxoacetate. The formation of a biaryl bond by Suzuki-Miyaura coupling reaction, followed by the hydrolysis of the ester, gave a biaryloxoacetic acid. Treatment of this acid with CDI gave the corresponding imidazolide. The ring closure to the desired phenanthrenequinone was accomplished by intramolecular Friedel-Crafts reaction of the imidazolide promoted by TiCl4.

  DOI：

  10.1021/ol071261h

文献信息

• An Efficient and Scalable Synthesis of Substituted Phenanthrenequinones by Intramolecular Friedel−Crafts Reaction of Imidazolides
  作者：Naoki Yoshikawa、Austin Doyle、Lushi Tan、Jerry A. Murry、Atsushi Akao、Masashi Kawasaki、Kimihiko Sato

  DOI：10.1021/ol071261h

  日期：2007.10.1

  An efficient synthesis of 9,10-phenanthrenequinones is described. The two carbonyl groups were introduced by an orthoselective intermolecular Friedel-Crafts reaction of 3-methoxyphenol with ethyl chlorooxoacetate. The formation of a biaryl bond by Suzuki-Miyaura coupling reaction, followed by the hydrolysis of the ester, gave a biaryloxoacetic acid. Treatment of this acid with CDI gave the corresponding imidazolide. The ring closure to the desired phenanthrenequinone was accomplished by intramolecular Friedel-Crafts reaction of the imidazolide promoted by TiCl4.