2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)acetamide | 144181-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)acetamide
• CAS: 144181-61-3
• 化学式: C₉H₈F₃NO₂
• mdl: MFCD24392335
• 分子量: 219.163
• InChiKey: BDDPAXWEOTUNHU-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  281.8±40.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)acetamide 在 氨 作用下， 以 甲醇 、 苯 为溶剂， 反应 40.0h， 生成 7,16-bis(3-amino-2-hydroxy-5-methylbenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  参考文献：
  名称：

  Diaza-18-Crown-6 Ligands Containing Two Aminophenol Side Arms:  New Heterobinuclear Metal Ion Receptors

  摘要：

  Three diaza-18-crown-6 ligands substituted with two aminophenol side arms were synthesized as possible heterobinuclear metal ion receptors. Bis(p-aminophenol)-substituted diaza-18-crown-6 ligand (13) was prepared by treating the diazacrown with alpha-bromo-4-nitro-o-cresol in the presence of N,N-diisopropylethylamine followed by reduction of the nitro groups. Bis(o-aminophenol)substituted diaza-18-crown-6 ligands (11 and 12) were prepared in two steps by the aminomethylation of either an o-nitrophenol or o-(trifluoroacetamido)phenol followed by reduction of the nitro groups or hydrolysis of the trifluoroacetamide groups. All new bisphenol-armed diazacrown ligands were purified by ultrasonication in MeOH followed by filtration and drying. Interaction of the ligands with Na+, K+, Ag+, and Cu2+ was evaluated by a calorimetric titration technique at 25 degrees C in MeOH. The complexes of Ag+ and Cu2+ much more stable than those of Na+ and K+. Heterobinuclear complexes were observed for 11-Cu2+- Na+ and 12-Cu2+-Na+ but not for 13-Cu2+-Na+ or for 12-Cu2+-Ag+.

  DOI：

  10.1021/jo9816212
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)acetamide
  参考文献：
  名称：

  Diaza-18-Crown-6 Ligands Containing Two Aminophenol Side Arms:  New Heterobinuclear Metal Ion Receptors

  摘要：

  Three diaza-18-crown-6 ligands substituted with two aminophenol side arms were synthesized as possible heterobinuclear metal ion receptors. Bis(p-aminophenol)-substituted diaza-18-crown-6 ligand (13) was prepared by treating the diazacrown with alpha-bromo-4-nitro-o-cresol in the presence of N,N-diisopropylethylamine followed by reduction of the nitro groups. Bis(o-aminophenol)substituted diaza-18-crown-6 ligands (11 and 12) were prepared in two steps by the aminomethylation of either an o-nitrophenol or o-(trifluoroacetamido)phenol followed by reduction of the nitro groups or hydrolysis of the trifluoroacetamide groups. All new bisphenol-armed diazacrown ligands were purified by ultrasonication in MeOH followed by filtration and drying. Interaction of the ligands with Na+, K+, Ag+, and Cu2+ was evaluated by a calorimetric titration technique at 25 degrees C in MeOH. The complexes of Ag+ and Cu2+ much more stable than those of Na+ and K+. Heterobinuclear complexes were observed for 11-Cu2+- Na+ and 12-Cu2+-Na+ but not for 13-Cu2+-Na+ or for 12-Cu2+-Ag+.

  DOI：

  10.1021/jo9816212

文献信息

• CH Oxygenation and<i>N</i>-Trifluoroacylation of Arylamines Under Metal-Free Conditions: A Convenient Approach to 2-Aminophenols and<i>N</i>-Trifluoroacyl-<i>ortho</i>-aminophenols
  作者：Vunnam Venkateswarlu、K. A. Aravinda Kumar、Shilpi Balgotra、G. Lakshma Reddy、M. Srinivas、Ram A. Vishwakarma、Sanghapal D. Sawant

  DOI：10.1002/chem.201402411

  日期：2014.5.26

  Direct ortho‐hydroxylation through CH oxygenation and N‐trifluoroacylation of anilines was achieved in a single step under metal‐free conditions by using a combination of TFA and oxone. The method allowed the formation of functionalised amino phenolic compounds such as ortho‐hydroxy‐N‐trifluoroacetanilides in good yields with broad substrate scope.

  通过在无金属条件下，通过使用TFA和过硫酸氢钾的组合，一步实现苯胺的CH 3 H氧化和N-三氟酰化直接邻羟基化。该方法可以形成功能化的氨基酚类化合物，例如邻-羟基-N-三氟乙酰苯胺，收率高，具有广泛的底物范围。
• Benzoxazine derivatives and their application in therapy
  申请人：Synthelabo

  公开号：US05447928A1

  公开（公告）日：1995-09-05

  Compounds of the formula ##STR1## in which Y represents hydrogen, fluorine, chlorine, methyl or methoxy, R.sub.1 represents phenyl substituted by fluorine, methyl, methoxy, trifluoromethyl or phenyl, or R.sub.1 represents 2-thienyl, R.sub.2 represents methyl, and R.sub.3 represents (C.sub.1 -C.sub.4)-alkyl, or phenyl-(C.sub.1 -C.sub.2)-alkyl optionally substituted on the ring by 2 to 3 methoxy groups, or 2-(2-pyridyl)ethyl, or R.sub.2 and R.sub.3 form, with the adjacent nitrogen, 4-phenyl(1-piperidyl), 4-phenylmethyl(1-piperidyl), 1,2,3,4-tetrahydro-2-isoquinolyl, 6-methoxy-1,2,3,4-tetrahydro-2-isoquinolyl, 5,8-dimethoxy-1,2,3,4-tetrahydro-2-isoquinolyl, 6,7-dimethoxy 1,2,3,4-tetrahydro-2-isoquinolyl, 2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl, or 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl, and X represents carbonyl or sulphonyl, and their salts are useful as neuroprotective and antiiischaemic agents.

  式##STR1##化合物，其中Y代表氢、氟、氯、甲基或甲氧基，R1代表被氟、甲基、甲氧基、三氟甲基或苯基取代的苯基，或者R1代表2-噻吩基，R2代表甲基，R3代表(C1-C4)烷基，或苯基-(C1-C2)烷基，环上可选择性地被2至3个甲氧基取代，或2-(2-吡啶基)乙基，或者R2和R3与相邻的氮原子一起形成4-苯基(1-哌啶基)、4-苯甲基(1-哌啶基)、1,2,3,4-四氢-2-异喹啉基、6-甲氧基-1,2,3,4-四氢-2-异喹啉基、5,8-二甲氧基-1,2,3,4-四氢-2-异喹啉基、6,7-二甲氧基1,2,3,4-四氢-2-异喹啉基、2,3,4,5-四氢-1H-3-苯并氮杂环庚三烯-3-基，或7,8-二甲氧基-2,3,4,5-四氢-1H-3-苯并氮杂环庚三烯-3-基，X代表羰基或磺酰基，及其盐类，可用作神经保护和抗缺血药物。
• 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.
• 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.
• Direct C–N bond cleavage of N-vinyl or N-allyl arylamines: a metal-free strategy for N-devinylation and N-deallylation
  作者：Shilpi Balgotra、Vunnam Venkateswarlu、Ram A. Vishwakarma、Sanghapal D. Sawant

  DOI：10.1016/j.tetlet.2015.05.042

  日期：2015.7

  A simple and convenient N-devinylation and N-deallylation strategy for N-vinyl and N-allyl arylamines in the presence of TFA/oxone is presented with the formation of selective ortho-hydroxylated and N-triflu-oroacylated arylamine product in good yields. This method is important for protection/deprotection of arylamines in organic synthesis and useful as a medicinal chemistry tool at late stage modifications in drug discovery programs. (c) 2015 Elsevier Ltd. All rights reserved.