1,3-dimethoxy-2,4,5-trifluorbenzene | 195136-70-0

• 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: 1,3-dimethoxy-2,4,5-trifluorbenzene
• 英文别名: 1,2,4-Trifluoro-3,5-dimethoxybenzene
• CAS: 195136-70-0
• 化学式: C₈H₇F₃O₂
• 分子量: 192.138
• InChiKey: AXSBVNAPIRNPHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-2,4,5-trifluorbenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2,4,5-Trifluororesorcinol
  参考文献：
  名称：

  Synthesis of Fluorinated Fluoresceins

  摘要：

  Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)-nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4-difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pK(a) = 3.3-6.1) than fluorescein (pK(a) = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85-0.97), which, in combination with their lower pK(a)s and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.

  DOI：

  10.1021/jo9706178
• 作为产物：
  描述：

  五氟硝基苯 在 palladium on activated charcoal 盐酸 、 氢气 、 亚膦酸 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 4.0~20.0 ℃ 、275.79 kPa 条件下， 反应 2.25h， 生成 1,3-dimethoxy-2,4,5-trifluorbenzene
  参考文献：
  名称：

  Synthesis of Fluorinated Fluoresceins

  摘要：

  Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)-nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4-difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pK(a) = 3.3-6.1) than fluorescein (pK(a) = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85-0.97), which, in combination with their lower pK(a)s and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.

  DOI：

  10.1021/jo9706178

文献信息

• US6162931A
  申请人：——

  公开号：US6162931A

  公开（公告）日：2000-12-19
• US6229055B1
  申请人：——

  公开号：US6229055B1

  公开（公告）日：2001-05-08