1-Amino-2,4-dimethoxy-3,5,6-trifluorobenzene | 2010-71-1

• 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-Amino-2,4-dimethoxy-3,5,6-trifluorobenzene
• 英文别名: 2,3,5-Trifluoro-4,6-dimethoxyaniline
• CAS: 2010-71-1
• 化学式: C₈H₈F₃NO₂
• 分子量: 207.152
• InChiKey: YMKBRJMLFYGEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  44.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-Amino-2,4-dimethoxy-3,5,6-trifluorobenzene 在 盐酸 、 亚膦酸 、 sodium nitrite 作用下， 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
• 作为产物：
  描述：

  五氟硝基苯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 生成 1-Amino-2,4-dimethoxy-3,5,6-trifluorobenzene
  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

• Fluorinated xanthene derivatives
  申请人：Molecular Probes, Inc.

  公开号：US06162931A1

  公开（公告）日：2000-12-19

  The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.

  该发明的染料家族是直接在一个或多个芳香碳上被氟取代的荧光素和罗丹素。这些氟取代的荧光染料具有更高的光稳定性，在生理范围为6-8的pH变化下比非氟化染料具有较低的敏感性，当与物质结合时表现出较少的猝灭，并具有额外的优势。该发明的染料可用作可检测的示踪剂，并用于制备有机和无机物质的共轭物。
• 472. Aromatic polyfluoro-compounds. Part XXIII. Polyfluoroazo, -azoxy-, and -hydrazo-benzenes
  作者：J. Burdon、C. J. Morton、D. F. Thomas

  DOI：10.1039/jr9650002621

  日期：——
• 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