3-acetyl-2-hydroxy-5-methoxy-4-phenyl-2-(trifluoromethyl)chromane | 1423130-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-acetyl-2-hydroxy-5-methoxy-4-phenyl-2-(trifluoromethyl)chromane
• 英文别名: 5-methoxy-3,4-dihydro-2H-chromene；1-[2-Hydroxy-5-methoxy-4-phenyl-2-(trifluoromethyl)-3,4-dihydrochromen-3-yl]ethanone；1-[2-hydroxy-5-methoxy-4-phenyl-2-(trifluoromethyl)-3,4-dihydrochromen-3-yl]ethanone
• CAS: 1423130-83-9
• 化学式: C₁₉H₁₇F₃O₄
• 分子量: 366.337
• InChiKey: AOHHEQHYSIWCML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲醇 、 3-acetyl-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one 在 碘 作用下， 反应 16.0h， 以89%的产率得到3-acetyl-2-hydroxy-5-methoxy-4-phenyl-2-(trifluoromethyl)chromane
  参考文献：
  名称：

  Efficient entry to trifluoromethyl substituted chromanes from oxidative aromatization of tetrahydro-2H-chromen-5(6H)-ones using iodine/alcohol with conventional and microwave methods

  摘要：

  This paper describes the one-pot simple and efficient oxidative aromatization reaction employing an iodine/alcohol medium for the preparation of a series of 11 new 3-acyl-2-hydroxy-5-alkoxy-4-aryl-2-(trifluoromethyl)chromanes, where acyl = Ac, Bz, furan-2-oyl; aryl = Ph, 4-NO2C6H4, 4-OCH3C6H4 and alkoxy = OMe, O-Pr-n, EtO and OBn from the respective 3-acyl-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones. Yields in the range of 50-89% were obtained when the oxidative reactions were performed using both conventional thermal heating (CTH) and microwave (MW) procedures. In general, the MW method produced similar yields with shorter reaction times and easier reaction workups. As an example, a representative X-ray diffraction ORTEP for 3-benzoyl-2-hydroxy-5-methoxy-4-methoxyphenyl-2-(trifluoromethyl)chromane is also shown. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.024