N-(5-fluoro-2-hydroxyphenyl)trifluoroacetamide | 144191-87-7

• 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: N-(5-fluoro-2-hydroxyphenyl)trifluoroacetamide
• 英文别名: 2,2,2-trifluoro-N-(5-fluoro-2-hydroxyphenyl)acetamide
• CAS: 144191-87-7
• 化学式: C₈H₅F₄NO₂
• 分子量: 223.127
• InChiKey: ZPGMBNMIELOUBK-UHFFFAOYSA-N

物化性质

• 沸点：
  281.2±40.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-溴巴豆酸乙酯 、 N-(5-fluoro-2-hydroxyphenyl)trifluoroacetamide 在 sodium hydroxide 、 sodium 作用下， 以 乙醇 、 水 为溶剂， 生成 ethyl (+/-)-6-fluoro-3,4-dihydro-2H-1,4-benzoxazine-3-acetate
  参考文献：
  名称：

  3-(2-aminomethyl)-4-[3-trifluoromethyl)benzoyl]-3-4

  摘要：

  通式(I)的化合物##STR1##，其中R.sub.1代表氢、氟或氯原子或甲基、C.sub.1 -C.sub.3烷氧基或硝基；R.sub.3代表氢原子或C.sub.1 -C.sub.3烷基；R.sub.4代表2,3-二氢-1H-茚-2-基、2,3-二氢-1H-茚-1-基或1,2,3,4-四氢萘-1-基；或者R.sub.3和R.sub.4与它们连接的氮原子共同构成1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚-2-基、1,2,3,4-四氢-9H-吡啶并[4,3-b]吲哚-3-基、4,5,6,7-四氢噻吩并[2,3-c]吡啶-6-基、4,5,6,7-四氢噻吩并[3,2-c]吡啶-6-基或2,3-二氢-1H-异吲哚-2-基；对于治疗和预防脑部疾病很有用。

  公开号：

  US05550125A1
• 作为产物：
  描述：

  2,5-二氟苯胺 、 三氟乙酸 在 Oxone 作用下， 以 1,4-二氧六环 为溶剂， 以67%的产率得到N-(5-fluoro-2-hydroxyphenyl)trifluoroacetamide
  参考文献：
  名称：

  Metal-Free Chemoselective ortho-C(sp2)–F Bond Hydroxylation and N-Trifluoroacylation of Fluoroarylamines for Domino Synthesis of 2-(N-Trifluoroacyl)aminophenols

  摘要：

  A novel chemoselective reaction for the formation of C-O bonds by C(sp(2))-F bond cleavage and concomitant N-trifluoroacylation of fluoroanilines using trifluoroacetic acid and Oxone((R)) is presented. This domino reaction gives o-hydroxy-N-trifluoroacetanilides in good yields under metal-free conditions in a single step. Selective ortho-directed monohydroxylation and N-trifluoroacylation of 2- and 6-fluoro- or 2,6-difluoro-substituted anilines takes place in this transformation.

  DOI：

  10.1055/s-0034-1379905

文献信息

• Dérivés de 3-(2-aminoéthyl)-4-(3-(trifluorométhyl)benzoyl)-3,4-dihydro-2H-1,4-benzoxazine, leur préparation et leur application en thérapeutique
  申请人：SYNTHELABO

  公开号：EP0666260A1

  公开（公告）日：1995-08-09

  Composés répondant à la formule générale (I) dans laquelle R₁ représente un atome d'hydrogène, de fluor ou de chlore ou un groupe méthyle, alcoxy en C₁-C₃ ou nitro, R₃ représente un atome d'hydrogène ou un groupe alkyle en C₁-C₃, R₄ représente un groupe 2,3-dihydro-1H-indén-2-yle, 2,3-dihydro-1H-indén-1-yle ou 1,2,3,4-tétrahydronaphtalén-1-yle, ou bien R₃ et R₄ forment, avec l'atome d'azote, un groupe 1,2,3,4-tétrahydro-9H-pyrido[3,4-b]indol-2-yle, 1,2,3,4-tétrahydro-9H-pyrido[4,3-b]indol-3-yle, 4,5,6,7-tétrahydrothiéno[2,3-c]pyridin-6-yle, 4,5,6,7-tétrahydrothiéno[3,2-c]pyridin-6-yle ou 2,3-dihydro-1H-isoindol-2-yle.

  通式(I)对应的化合物 其中 R₁ 代表氢原子、氟原子或氯原子或甲基、C₁-C₃ 烷氧基或硝基，R₃ 代表氢原子或 C₁-C₃ 烷基，R₄ 代表 2,3-二氢-1H-茚-2-基、2,3-二氢-1H-茚-1-基或 1,2,3、4-四氢萘-1-基，或 R₃ 和 R₄ 与氮原子一起形成 1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚-2-基、1,2,3、4-tétrahydro-9H-pyrido[4,3-b]indol-3-yle, 4,5,6,7-tétrahydrothiéno[2,3-c]pyridin-6-yle, 4,5,6,7-tétrahydrothiéno[3,2-c]pyridin-6-yle ou 2,3-dihydro-1H-isoindol-2-yle.
• Acid-catalyzed amino-migration of O-phenylhydroxylamines
  作者：Naoki Haga、Yasuyuki Endo、Kenichiro Kataoka、Kentaro Yamaguchi、Koichi Shudo

  DOI：10.1021/ja00051a012

  日期：1992.12

  The mechanism of amino-migration of O-phenylhydroxylamine (1a) was studied. It was found that 1 rearranges to give 2-aminophenol (50%) and 4-aminophenol (7%) in trifluoroacetic acid (TFA). The predominance of the ortho rearrangement of 1 clearly distinguishes this process from the Bamberger rearrangement. From cross-coupling experiments employing stable isotopes, it was clarified that the ortho rearrangement proceeds intramolecularly and the para rearrangement involves both intra- and intermolecular processes. Good first-order kinetics were obtained for the rearrangement. The Hammett plot (sigma+) with a large negative slope (rho = -7.8) indicates that initial heterolytic N-O bond cleavage of 1 occurs and generates a positive charge on the oxygen atom with considerable delocalization into the aromatic ring. An ion-molecule pair involving a phenoxenium ion and an ammonia molecule as an intermediate rationalizes all of the results. In this pair, intramolecular combination to the ortho position proceeds preferentially over that to the para position. Formation of catechol and hydroquinone can be explained in terms of nucleophilic attack of TFA on the phenoxenium ion in a solvent-separated pair.
• US5550125A
  申请人：——

  公开号：US5550125A

  公开（公告）日：1996-08-27
• Metal-Free Chemoselective ortho-C(sp2)–F Bond Hydroxylation and N-Trifluoroacylation of Fluoroarylamines for Domino Synthesis of 2-(N-Trifluoroacyl)aminophenols
  作者：Sanghapal Sawant、Vunnam Venkateswarlu、Shilpi Balgotra、K. Aravinda Kumar、Ram Vishwakarma

  DOI：10.1055/s-0034-1379905

  日期：——

  A novel chemoselective reaction for the formation of C-O bonds by C(sp(2))-F bond cleavage and concomitant N-trifluoroacylation of fluoroanilines using trifluoroacetic acid and Oxone((R)) is presented. This domino reaction gives o-hydroxy-N-trifluoroacetanilides in good yields under metal-free conditions in a single step. Selective ortho-directed monohydroxylation and N-trifluoroacylation of 2- and 6-fluoro- or 2,6-difluoro-substituted anilines takes place in this transformation.
• 3-(2-aminomethyl)-4-[3-trifluoromethyl)benzoyl]-3-4
  申请人：Synthelabo

  公开号：US05550125A1

  公开（公告）日：1996-08-27

  Compounds of the general formula (I) ##STR1## wherein R.sub.1 represents a hydrogen, fluorine or chlorine atom or a methyl, C.sub.1 -C.sub.3 alkoxy or nitro group; R.sub.3 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sub.4 represents a 2,3-dihydro-1H-inden-2-yl, 2,3-dihydro-1H-inden-1-yl or 1,2,3,4-tetrahydronaphthalen-1-yl group; or alternatively R.sub.3 and R.sub.4 complete, with the nitrogen atom to which they are attached, a 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indol-2-yl, 1,2,3,4-tetrahydro-9H-pyrido[4,3-b]indol-3-yl, 4,5,6,7-tetrahydrothieno[2,3-c]pyrid-6-yl, 4,5,6,7-tetrahydrothieno[3,2-c]pyrid-6-yl or 2,3-dihydro-1H-isoindol-2-yl group; are useful for the treatment and prevention of cerebral disorders.

  通式(I)的化合物##STR1##，其中R.sub.1代表氢、氟或氯原子或甲基、C.sub.1 -C.sub.3烷氧基或硝基；R.sub.3代表氢原子或C.sub.1 -C.sub.3烷基；R.sub.4代表2,3-二氢-1H-茚-2-基、2,3-二氢-1H-茚-1-基或1,2,3,4-四氢萘-1-基；或者R.sub.3和R.sub.4与它们连接的氮原子共同构成1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚-2-基、1,2,3,4-四氢-9H-吡啶并[4,3-b]吲哚-3-基、4,5,6,7-四氢噻吩并[2,3-c]吡啶-6-基、4,5,6,7-四氢噻吩并[3,2-c]吡啶-6-基或2,3-二氢-1H-异吲哚-2-基；对于治疗和预防脑部疾病很有用。