5-(Difluoromethyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-ol | 339322-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(Difluoromethyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-ol
• 英文别名: 5-(difluoromethyl)-3-(2-hydroxyphenyl)-4H-1,2-oxazol-5-ol
• CAS: 339322-22-4
• 化学式: C₁₀H₉F₂NO₃
• 分子量: 229.183
• InChiKey: ZZOQCZPOSYUYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(Difluoromethyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-ol 在 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以72%的产率得到2-[5-(difluoromethyl)-3-isoxazolyl]phenol
  参考文献：
  名称：

  摘要：

  The reactions of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydroxylamine yield, through Delta(2)-isoxazolines as intermediate products, 3-(2-hydroxyaryl)-5-polyfluoroalkylisoxazoles. Analogous reactions with 2-polyfluoroalkylchromones afford beta-diketone monooximes, which in an acidic medium undergo cyclode hydration into 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles. The structures of regioisomeric 3- and 5-polyfluoroalkylisoxazoles were determined using H-1, F-19, and C-13 NMR spectroscopy.

  DOI：

  10.1023/a:1020908831426
• 作为产物：
  描述：

  2-(difluoromethyl)-4-chromenone 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 5-(Difluoromethyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-ol 、
  参考文献：
  名称：

  摘要：

  The reactions of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydroxylamine yield, through Delta(2)-isoxazolines as intermediate products, 3-(2-hydroxyaryl)-5-polyfluoroalkylisoxazoles. Analogous reactions with 2-polyfluoroalkylchromones afford beta-diketone monooximes, which in an acidic medium undergo cyclode hydration into 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles. The structures of regioisomeric 3- and 5-polyfluoroalkylisoxazoles were determined using H-1, F-19, and C-13 NMR spectroscopy.

  DOI：

  10.1023/a:1020908831426

文献信息

• [EN] SUBSTITUTED ISOXALINES, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, METHODS OF PREPARING SAME, AND USES OF SAME<br/>[FR] ISOXAZOLINES SUBSTITUÉES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, PROCÉDÉS DE PRÉPARATION DE CELLES-CI ET UTILISATIONS DE CELLES-CI
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2008006561A1

  公开（公告）日：2008-01-17

  [EN] The invention relates to substituted isoxazolines according to the general formula (I) : in which A, R1, R2, R3, R4, Z, X, m, n, and p, are given in the claims, and salts thereof, to pharmaceutical compositions comprising said substituted isoxazolines, to methods of preparing said substituted isoxazolines as well as the use thereof for manufacturing a pharmaceutical composition for the treatment of diseases known to be at least in part mediated by HDAC activity or whose symptoms are known to be alleviated by HDAC inhibitors.
  [FR] L'invention concerne des isoxazolines substituées de formule générale (I) dans laquelle A, R1, R2, R3, R4, Z, X, m, n et p sont tels que définis dans les revendications, ainsi que des sels de celles-ci, des compositions pharmaceutiques comprenant lesdites isoxazolines substituées, des procédés de préparation desdites isoxazolines substituées, de même que l'utilisation de celles-ci pour la fabrication d'une composition pharmaceutique destinée au traitement de maladies connues pour être au moins pour partie à médiation par l'activité de l'HDAC ou dont on sait que les symptômes sont soulagés par les inhibiteurs de l'HDAC.
• ——
  作者：V. Ya. Sosnovskikh、A. Yu. Sizov、B. I. Usachev

  DOI：10.1023/a:1020908831426

  日期：——

  The reactions of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydroxylamine yield, through Delta(2)-isoxazolines as intermediate products, 3-(2-hydroxyaryl)-5-polyfluoroalkylisoxazoles. Analogous reactions with 2-polyfluoroalkylchromones afford beta-diketone monooximes, which in an acidic medium undergo cyclode hydration into 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles. The structures of regioisomeric 3- and 5-polyfluoroalkylisoxazoles were determined using H-1, F-19, and C-13 NMR spectroscopy.