3-乙氧基-2,4,5-三氟苯甲酸 | 169507-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-乙氧基-2,4,5-三氟苯甲酸
• 中文别名: 2,4,5-三氟-3-乙氧基苯甲酸
• 英文名称: 3-ethoxy-2,4,5-trifluorobenzoic acid
• CAS: 169507-61-3
• 化学式: C₉H₇F₃O₃
• 分子量: 220.148
• InChiKey: HXAPHOPNZQFBEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  297.4±35.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-乙氧基-2,4,5-三氟苯甲酸 在 镍 2,2'-联吡啶 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 硫酸 、 氢气 、 乙酸酐 、 sodium hydride 、 potassium nitrate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， -30.0~30.0 ℃ 、206.84 kPa 条件下， 反应 101.0h， 生成 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

  摘要：

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.

  DOI：

  10.1021/jm00022a013
• 作为产物：
  描述：

  2,4,5-三氟-3-羟基苯甲酸 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-乙氧基-2,4,5-三氟苯甲酸
  参考文献：
  名称：

  The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

  摘要：

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.

  DOI：

  10.1021/jm00022a013

文献信息

• Process for the preparation of 4-alkoxy-3,5,6-trifluoro-phthalic acids
  申请人：Hoechst Aktiengesellschaft

  公开号：US05488152A1

  公开（公告）日：1996-01-30

  The present invention relates to a process for the preparation of 4-alkoxy-3,5,6-trifluorophthalic acids of the formula ##STR1## in which R is an alkyl radical having 1 to 5 carbon atoms which may be monofluorinated or polyfluorinated, a cycloalkyl radical having 3 to 5 carbon atoms in the ring which may be monofluorinated or polyfluorinated, or an araliphatic radical which may be monofluorinated or polyfluorinated, or, if desired, of 3-alkoxy-2,4,5-trifluorobenzoic acids of the formula ##STR2## in which R is as defined above, which involves reacting tetrafluorophthalic acid or tetrafluorophthalic anhydride with an alcohol of the formula ROH in which R is as defined above and with a water-soluble base in water at elevated temperature, isolating the 4-alkoxy-3,5,6-trifluorophthalic acid formed and, if desired, decarboxylating the 4-alkoxy-3,5,6-trifluorophthalic acid in the presence of a basic solvent and, if desired, of an inert solvent at from 70.degree. to 180.degree. C., and isolating the 3-alkoxy-2,4,5-trifluorobenzoic acid formed.

  本发明涉及一种制备式为##STR1##的4-烷氧基-3,5,6-三氟苯甲酸的过程，其中R是具有1至5个碳原子的烷基基团，可单氟化或多氟化，具有3至5个碳原子的环烷基基团，可单氟化或多氟化，或是可单氟化或多氟化的芳基烷基基团，或者如所需的那样，式为##STR2##的3-烷氧基-2,4,5-三氟苯甲酸的制备方法，其中R如上所定义，包括将四氟苯甲酸或四氟苯甲酸酐与ROH的醇反应，其中R如上所定义，并与水溶性碱在水中高温反应，分离所形成的4-烷氧基-3,5,6-三氟苯甲酸，并在碱性溶剂和如所需的惰性溶剂的存在下，在70℃至180℃的温度下，如所需的那样脱羧，分离所形成的3-烷氧基-2,4,5-三氟苯甲酸。
• Verfahren zur Herstellung von 4-Alkoxy-3,5,6-trifluorphthalsäuren und 3-Alkoxy-2,4,5-trifluorbenzoesäuren
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0667334A2

  公开（公告）日：1995-08-16

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von 4-Alkoxy-3,5,6-trifluorphthalsäuren der allgemeinen Formel worin R für einen gegebenenfalls einfach oder mehrfach fluorierten Alkylrest mit 1 bis 5 Kohlenstoffatomen, für einen gegebenenfalls einfach oder mehrfach fluorierten Cycloalkylrest mit 3 bis 5 Kohlenstoffatomen im Ring oder für einen gegebenenfalls einfach oder mehrfach fluorierten araliphatischen Rest steht, und gegebenenfalls von 3-Alkoxy-2,4,5-trifluorbenzoesäure der allgemeinen Formel worin R die vorstehende Bedeutung hat, indem man Tetrafluorphthalsäure oder Tetrafluorphthalsäureanhydrid mit einem Alkohol der allgemeinen Formel ROH, worin R die vorstehende Bedeutung hat, und einer wasserlöslichen Base in Wasser bei erhöhter Temperatur umsetzt, die gebildete 4-Alkoxy-3,5,6-trifluorphthalsäure isoliert und gegebenenfalls die 4-Alkoxy-3,5,6-trifluorphthalsäure in Anwesenheit eines basischen Lösungsmittels und gegebenenfalls eines inerten Lösungsmittels bei 70 bis 180 °C decarboxyliert und die gebildete 3-Alkoxy-2,4,5-trifluorbenzoesäure isoliert.

  本发明涉及一种通式为 4-烷氧基-3,5,6-三氟邻苯二甲酸的制备方法。 其中 R 代表具有 1 至 5 个碳原子的任选单氟或多氟烷基、环中具有 3 至 5 个碳原子的任选单氟或多氟环烷基或任选单氟或多氟脂肪族基，以及通式为 3-烷氧基-2,4,5-三氟苯甲酸的任选 3-烷氧基-2,4,5-三氟苯甲酸。 将四氟邻苯二甲酸或四氟邻苯二甲酸酐与通式为 ROH（其中 R 具有上述含义）的醇和水溶性碱在高温下在水中反应，得到 4-烷氧基-3、分离出 4-烷氧基-3,5,6-三氟邻苯二甲酸，并酌情在碱性溶剂和惰性 溶剂（如适用）存在下，在 70 至 180℃下对 4-烷氧基-3,5,6-三氟邻苯二甲酸进行脱羧，分离出形成的 3-烷氧基-2,4,5-三氟苯甲酸。
• Processes for producing tetrafluorophtahlic anhydride and fluorobenzoic acids
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0669310A1

  公开（公告）日：1995-08-30

  A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3H]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.

  一种生产四氟邻苯二甲酸酐的工艺，包括将四氯邻苯二甲酸酐氯化以获得 3,3,4,5,6,7-六氯-1-[3H]-异苯并呋喃酮，然后将其氟化以获得 3,4,5,6-四氟邻苯二甲酸二氟化物和/或 3、3,4,5,6,7-六氟-1-[3H]-异苯并呋喃酮，再将四氟邻苯二氟化物和/或六氟-1-[3H]-异苯并呋喃酮与无机碱或有机酸反应，得到四氟邻苯二甲酸酐。
• Processes for producing tetra-fluorophthalic anhydride and fluorobenzioc acids
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0866050A1

  公开（公告）日：1998-09-23

  A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3H]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.

  一种生产四氟邻苯二甲酸酐的工艺，包括将四氯邻苯二甲酸酐氯化以获得 3,3,4,5,6,7-六氯-1-[3H]-异苯并呋喃酮，然后将其氟化以获得 3,4,5,6-四氟邻苯二甲酸二氟化物和/或 3、3,4,5,6,7-六氟-1-[3H]-异苯并呋喃酮，再将四氟邻苯二氟化物和/或六氟-1-[3H]-异苯并呋喃酮与无机碱或有机酸反应，得到四氟邻苯二甲酸酐。
• Processes for producing tetra-fluorophthalic anhydride and fluorobenzoic acids
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0877011A1

  公开（公告）日：1998-11-11

  A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3H]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.

  一种生产四氟邻苯二甲酸酐的工艺，包括将四氯邻苯二甲酸酐氯化以获得 3,3,4,5,6,7-六氯-1-[3H]-异苯并呋喃酮，然后将其氟化以获得 3,4,5,6-四氟邻苯二甲酸二氟化物和/或 3、3,4,5,6,7-六氟-1-[3H]-异苯并呋喃酮，再将四氟邻苯二氟化物和/或六氟-1-[3H]-异苯并呋喃酮与无机碱或有机酸反应，得到四氟邻苯二甲酸酐。