(4-fluoro-2-nitro-phenoxy)-acetic acid | 396-15-6

• 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: (4-fluoro-2-nitro-phenoxy)-acetic acid
• 英文别名: (4-Fluor-2-nitro-phenoxy)-essigsaeure；4-Fluoro-2-nitrophenoxyacetic acid；2-(4-fluoro-2-nitrophenoxy)acetic acid
• CAS: 396-15-6
• 化学式: C₈H₆FNO₅
• 分子量: 215.138
• InChiKey: HJYGFQJZJGUBLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-fluoro-2-nitro-phenoxy)-acetic acid 在 盐酸 、 铁粉 作用下， 生成 6-氟-2H-1,4-苯并嗪-3(4H)-酮
  参考文献：
  名称：

  Aromatic Fluorine Compounds. VIII. Plant Growth Regulators and Intermediates^1,2

  摘要：

  DOI：

  10.1021/ja01510a021
• 作为产物：
  描述：

  4-氟苯氧乙酸 在 硫酸 、 硝酸 作用下， 生成 (4-fluoro-2-nitro-phenoxy)-acetic acid
  参考文献：
  名称：

  Aromatic Fluorine Compounds. VIII. Plant Growth Regulators and Intermediates^1,2

  摘要：

  DOI：

  10.1021/ja01510a021

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：SENEXIS LTD

  公开号：WO2011144578A1

  公开（公告）日：2011-11-24

  A compound of formula (I) or a pharmaceutically acceptable salt or prodrug thereof wherein X is N or CH; Q is NR6 or O; A1 and A2 are independently hydrogen or C1-6 alkyl or may together form a carbonyl group; R1 and R2 are independently hydrogen, halogen, CF3, CN, OR7, OR8, NR8R9, NR8COR10, NR8S02R10, S02NR8R9, SO2R10 or C1-6 alkyl optionally and independently substituted by one or more of hydroxyl, C1-6 alkoxy, halogen or NR8 R9; R 3 is hydrogen, halogen, CF3 or OR 7; R4 is hydrogen, halogen, CF3, OR8, NR8R9, NR8COR10, NR8S02R10 or C1-6 alkyl optionally substituted by hydroxyl, C1-6 alkoxy or NR 8 R 9; or when R3 and R4 are positioned ortho and taken together form -0(CH2)mO-, where m is 1-3; R5 is hydrogen or C1-6 alkyl optionally substituted by hydroxyl, C1-6 alkoxy or NR8 R9; R6 is hydrogen or C1-6 alkyl; R7 is hydrogen or C1-6 alkyl optionally substituted by OR8 or NR8R9; R8 is hydrogen, C1-6 alkyl, optionally substituted by hydroxyl or C1-6 alkoxy or C1-3 alkylphenyl wherein said phenyl group is optionally substituted by one or more substituents selected from halogen, C1-6 alkyl, CF3, OR7, NR8R9 or OCF3; or the groups R8 and R9 when they are attached to a nitrogen atom may together form a 5- or 6-membered ring which optionally contains one further heteroatom selected from NR7, S and O said 5 or 6 membered ring being optionally substituted by hydroxyl or C1-6 alkoxy; or the groups R8 and R9 when they are attached to a nitrogen atom may together form an azetidinyl ring optionally substituted by hydroxyl or C1-6 alkoxy; and R10 is C1-6 alkyl or a phenyl group optionally substituted by one or more substituents selected from halogen, C1-6 alkyl, CF3, OCF3 or OR7; and n is 1 or 2. The use of the compounds in treating amyloid disease is also disclosed.

  式（I）的化合物或其药学上可接受的盐或前药，其中X为N或CH；Q为NR6或O；A1和A2独立地为氢或C1-6烷基，或者可共同形成一个羰基团；R1和R2独立地为氢、卤素、CF3、CN、OR7、OR8、NR8R9、NR8COR10、NR8S02R10、S02NR8R9、SO2R10或C1-6烷基，可选地并独立地被一个或多个羟基、C1-6烷氧基、卤素或NR8R9取代；R3为氢、卤素、CF3或OR7；R4为氢、卤素、CF3、OR8、NR8R9、NR8COR10、NR8S02R10或C1-6烷基，可选地被羟基、C1-6烷氧基或NR8R9取代；或者当R3和R4位于邻位并共同形成-0(CH2)mO-时，其中m为1-3；R5为氢或C1-6烷基，可选地被羟基、C1-6烷氧基或NR8R9取代；R6为氢或C1-6烷基；R7为氢或C1-6烷基，可选地被OR8或NR8R9取代；R8为氢、C1-6烷基，可选地被羟基或C1-6烷氧基或C1-3烷基苯基取代，其中所述苯基可选地被一个或多个卤素、C1-6烷基、CF3、OR7、NR8R9或OCF3中的一种或多种取代基取代；或者当R8和R9连接到一个氮原子时，它们可共同形成一个含有一个进一步异原子（选自NR7、S和O）的5-或6-成员环，所述5-或6-成员环可选地被羟基或C1-6烷氧基取代；或者当R8和R9连接到一个氮原子时，它们可共同形成一个可选地被羟基或C1-6烷氧基取代的氮杂环戊烷环；R10为C1-6烷基或一个苯基，可选地被一个或多个卤素、C1-6烷基、CF3、OCF3或OR7中的一种或多种取代基取代；n为1或2。还公开了这些化合物在治疗淀粉样蛋白病中的用途。
• Photoaffinity labeling of the electroplax sodium channel with tetrodotoxin derivatives. II. Comparison of the photoreactivity of different photoactivable groups in the tetrodotoxin binding site.
  作者：Eiichi YOSHIDA、Hitoshi NAKAYAMA、Yasumaru HATANAKA、Yuichi KANAOKA

  DOI：10.1248/cpb.38.982

  日期：——

  Four photoactivable tetrodotoxin (TTX) derivatives and the corresponding tritiated compounds were synthesized and porified. The photoactivable groups introduced were a nitro-azidophenyl (NAP) group and a trifluoromethyl diazirinobenzoyl (TDB) group, as nitrene and carbene precursors, respectively, as well as two isomers of the fluoronitrophenoxy group, a new photpreactive group selective for nucleophiles. The binding affinities of the four derivatives to the sodium channel were similar to that of TTX, but the values of specific photoincorporation were unexpectedly low (up to 2.5%), suggesting that the photpactivable groups are likely to be oriented unfavorably for labeling reactions in the TTX binding site. Two of the labeled sodium channel proteins were purified and digested. Peptides labeled with TTXenNAP lost most of the label during high performance liquid chromatography in 0.1% trifluoroacetic acid-acetonitrile, while peptides labeled with TTXenTDB retained the labels during the procedures. The TTXenTDB-labeled peptides were eluted in four major fractions with 80% recovery of the amount applied on a reverse-phased C4 column.However, further purification is necessary to identify the labeled sites of the peptides.

  我们合成了四种光活化河豚毒素（TTX）衍生物和相应的三价化合物，并对其进行了孔化。引入的光活性基团是硝基叠氮苯基（NAP）基团和三氟甲基重氮基苯甲酰基（TDB）基团，分别作为腈和碳烯的前体，以及氟硝基苯氧基基团的两种异构体，这是一种对亲核物具有选择性的新光活性基团。这四种衍生物与钠通道的结合亲和力与 TTX 相似，但特定光诱导结合值却出乎意料地低（低至 2.5%），这表明光活性基团的方向可能不利于 TTX 结合位点的标记反应。对两种标记的钠通道蛋白进行了纯化和消化。用 TTXenNAP 标记的肽在 0.1% 三氟乙酸-乙腈高效液相色谱法中失去了大部分标记，而用 TTXenTDB 标记的肽在此过程中保留了标记。TTXenTDB标记的肽在反相C4色谱柱上被洗脱成四个主要馏分，回收率为80%。
• Dérivés hétérocycliques, leurs procédés de préparation,médicaments les contenant, utiles notamment comme inhibiteurs de l'aldose réductase
  申请人：LABORATOIRES UPSA

  公开号：EP0162776A2

  公开（公告）日：1985-11-27

  L'invention concerne de nouveaux composés de formule: Inhibiteurs de l'aldose réductase. Traitement de certaines complications du diabète.

  本发明涉及新的式化合物： 醛糖还原酶抑制剂。治疗糖尿病的某些并发症。
• 10.1039/d4cc02118e
  作者：Winter, Johannes、Lühr, Susan、Hochadel, Kyra、Gálvez-Vázquez, María de Jesús、Prenzel, Tobias、Schollmeyer, Dieter、Waldvogel, Siegfried R.

  DOI：10.1039/d4cc02118e

  日期：——

  The electrochemical reduction of nitroarenes allows direct access to manifold nitrogen containing heterocycles. This work reports the simple and direct electro-organic synthesis of 18 different examples of 2H,4H-4-hydroxy-1,4-benzoxazin-3-ones in up to 81% yield. The scalability of the method was demonstrated on a gram-scale.

  硝基芳烃的电化学还原允许直接获得多种含氮杂环。这项工作报道了 18 种不同的 2 H ,4 H -4-羟基-1,4-苯并恶嗪-3-酮的简单直接的有机电合成，产率高达 81%。该方法的可扩展性在克级上得到了证明。
• COMPOUNDS
  申请人：Treherne, Johnathan Mark

  公开号：EP2571872B1

  公开（公告）日：2014-12-31