4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid | 50734-07-1

• 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: 4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid
• 英文别名: 4-methylaminobenzoic acid trifluoroacetate；p-(N-methyltrifluoroacetamido)benzoic acid；p-[N-methyl N-(trifluoroacetyl)amino]benzoic acid；Benzoic acid, 4-[methyl(trifluoroacetyl)amino]-；4-[methyl-(2,2,2-trifluoroacetyl)amino]benzoic acid
• CAS: 50734-07-1
• 化学式: C₁₀H₈F₃NO₃
• 分子量: 247.174
• InChiKey: PFXPSQZNEJOAOP-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C
• 沸点：
  317.5±42.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-甲氨基苯甲酸	4-methylaminobenzoic acid	10541-83-0	C8H9NO2	151.165

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-[Methyl-(2,2,2-trifluoro-acetyl)-amino]-benzoic acid 2-trimethylsilanyl-ethyl ester	212118-14-4	C15H20F3NO3Si	347.409
  4-甲氨基苯甲酸	4-methylaminobenzoic acid	10541-83-0	C8H9NO2	151.165

反应信息

• 作为反应物：
  描述：

  4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 75.0h， 生成 N-(5-chloropyridine-2-yl)-2-[(4-methylaminophenylcarbonyl)amino]-5-methylbenzamide
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOSITIONS COMPRISING ANTICOAGULANT N-(5-CHLOROPYRIDINE-2-YL)-2-({4-[ETHANIMIDOIL(METHYL)AMINO]BENZOYL}AMINO)-5-METHYLBENZAMIDE
  [FR] COMPOSITIONS PHARMACEUTIQUES COMPRENANT UN ANTICOAGULANT N-(5-CHLOROPYRIDIN-2-YL)-2-({4- [ÉTHANIMIDOYL(MÉTHYL)AMINO]BENZOYL}AMINO)-5-MÉTHYLBENZAMIDE

  摘要：

  本发明涉及医学领域，特别是药理学领域，即用于治疗与增加的血栓形成有关的疾病的新型口服药物组合物。该组合物包括抗凝剂N-（5-氯吡啶-2-基）-2-（{4- [乙烯基氨基甲酰]氨基}苯甲酰）-5-甲基苯甲酰胺或其药学上可接受的盐，为因子Xa抑制剂和多萜醇，并通过肠溶涂层或胶囊保护不受酸性胃液的接触。该组合物具有高效性和生物利用度，可用于治疗和预防其特征为不良血栓形成的疾病。

  公开号：

  WO2017217895A1
• 作为产物：
  描述：

  4-甲氨基苯甲酸 、 三氟乙酸酐 反应 2.0h， 生成 4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOSITIONS COMPRISING ANTICOAGULANT N-(5-CHLOROPYRIDINE-2-YL)-2-({4-[ETHANIMIDOIL(METHYL)AMINO]BENZOYL}AMINO)-5-METHYLBENZAMIDE
  [FR] COMPOSITIONS PHARMACEUTIQUES COMPRENANT UN ANTICOAGULANT N-(5-CHLOROPYRIDIN-2-YL)-2-({4- [ÉTHANIMIDOYL(MÉTHYL)AMINO]BENZOYL}AMINO)-5-MÉTHYLBENZAMIDE

  摘要：

  本发明涉及医学领域，特别是药理学领域，即用于治疗与增加的血栓形成有关的疾病的新型口服药物组合物。该组合物包括抗凝剂N-（5-氯吡啶-2-基）-2-（{4- [乙烯基氨基甲酰]氨基}苯甲酰）-5-甲基苯甲酰胺或其药学上可接受的盐，为因子Xa抑制剂和多萜醇，并通过肠溶涂层或胶囊保护不受酸性胃液的接触。该组合物具有高效性和生物利用度，可用于治疗和预防其特征为不良血栓形成的疾病。

  公开号：

  WO2017217895A1

文献信息

• Method for controlling emesis with
  申请人：A. H. Robins Company, Incorporated

  公开号：US03966957A1

  公开（公告）日：1976-06-29

  A method is disclosed for controlling emesis utilizing N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides of the formula: ##SPC1## Wherein R is cycloalkyl, phenyl and phenyllower-alkyl; R.sup.1 is hydrogen, lower alkyl of 1 to 8 carbon atoms and phenyl; R.sup.2 is halogen, lower-alkyl, lower-alkoxy, amino, nitro, monoalkylamino, dialkylamino, mercaptomethyl, acetamido, sulfamoyl, cyano, hydroxy, benzyloxy, and trifluoromethyl; X is oxygen and sulfur; n is an integer from zero to three inclusive and pharmaceutically acceptable acid addition salts thereof. The benzamide compounds wherein R is cyclohexyl and R.sup.1 is lower-alkyl are particularly effective as antiemetics and have minimal side effects.

  本发明公开了一种利用N-(1-取代的-3-吡咯烷基)苯甲酰胺和硫代苯甲酰胺控制呕吐的方法，其通式为：##SPC1##，其中R为环烷基、苯基和苯基低级烷基；R1为氢、1至8个碳原子的低级烷基和苯基；R2为卤素、低级烷基、低级烷氧基、氨基、硝基、单烷基氨基、二烷基氨基、巯基甲基、乙酰氨基、磺酰氨基、氰基、羟基、苄氧基和三氟甲基；X为氧和硫；n为0至3的整数，以及其药学上可接受的酸加成盐。当R为环己基，R1为低级烷基时，这些苯甲酰胺化合物特别有效地作为止吐剂，且副作用最小。
• Supramolecular Catalysis of Ester and Amide Cleavage by a Dinuclear Barium(II) Complex
  作者：Roberta Cacciapaglia、Stefano Di Stefano、Erik Kelderman、Luigi Mandolini

  DOI：10.1002/(sici)1521-3773(19990201)38:3<348::aid-anie348>3.0.co;2-d

  日期：1999.2.1

  Five components spontaneously self-assemble to yield the productive complex 1, where one barium ion delivers an ethoxide to the carbonyl group of an amide substrate anchored by means of a distal carboxylate moiety to the other barium ion. High substrate specificity, fairly high reaction rates with catalytic turnover, and competitive inhibition by inert substrates are observed.

  五个组分自发地自组装以产生生产性配合物1，其中一个钡离子将乙醇盐传递到酰胺底物的羰基上，该酰胺底物通过远端羧酸根部分锚定到另一个钡离子上。观察到高的底物特异性，相当高的催化转化反应速率以及惰性底物的竞争性抑制作用。
• Simple and Practical Conversion of Benzoic Acids to Phenols at Room Temperature
  作者：Wenzhang Xiong、Qiu Shi、Wenbo H. Liu

  DOI：10.1021/jacs.2c07529

  日期：2022.8.31

  Phenols are important organic molecules because they have found widespread applications in many fields. Herein, an efficient and practical approach to prepare phenols from benzoic acids via simple organic reagents at room temperature is reported. This approach is compatible with various functional groups and heterocycles and can be easily scaled up. To demonstrate its synthetic utility, bioactive molecules

  酚类是重要的有机分子，因为它们在许多领域都有广泛的应用。本文报道了一种在室温下通过简单的有机试剂从苯甲酸制备酚类的有效实用方法。这种方法与各种官能团和杂环兼容，并且可以轻松放大。为了证明其合成效用，生物活性分子和不对称六芳基苯已通过利用这种转变作为战略步骤来制备。机理研究表明，关键的迁移步骤涉及游离碳正离子而不是自由基中间体。考虑到苯甲酸的丰富性和酚类的实用性，预计该方法将在有机合成中得到广泛的应用。
• [EN] URETHANES, UREAS, AMIDINES AND RELATED INHIBITORS OF FACTOR XA<br/>[FR] URÉTHANES, URÉES, AMIDINES ET INHIBITEURS APPARENTÉS DU FACTEUR XA
  申请人：TOVBIN DMITRY GENNADIEVICH

  公开号：WO2011108963A8

  公开（公告）日：2012-12-27
• Synthesis and Structure−Activity Relationships of 2-Pyrazinylcarboxamido- benzoates and β-Ionylideneacetamidobenzoates with Retinoidal Activity
  作者：Paul Jones、Gérald B. Villeneuve、Chengpei Fei、Josie DeMarte、Allison J. Haggarty、Khin Than Nwe、Deborah A. Martin、Anne-Marie Lebuis、Joshua M. Finkelstein、Barbara J. Gour-Salin、Tak Hang Chan、Brian R. Leyland-Jones

  DOI：10.1021/jm9801354

  日期：1998.7.1

  The structure-activity relationships of two series of novel retinoids (2-pyrazinylcarboxamidobenzoates and beta-ionylideneacetamidobenzoates) have been investigated by evaluating their ability to induce differentiation in both human promyelocytic leukemia (HL60) cells and mouse embryonal carcinoma (P19) cells. The most active compound (ED50 = 8.3 x 10(-9) M) of the 2-pyrazinylcarboxamidobenzoates is 4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylquinoxalyl)-carboxamido]benzoic acid (9u), while the most active analogue of the beta-ionylideneacetamidobenzoates is 4-[3-methyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-(2E,4E)-pentadienamido]benzoic acid (10a, ED50 = 3.2 x 10(-8) M). Our studies identify an absolute requirement for the carboxylic acid moiety on the aromatic ring to be para relative to the amide linkage for activity. Benzoate substitutions in the ortho position relative to the terminal carboxylate (9d,k,r) are well-tolerated; however, a methoxy substituent meta relative to the terminal carboxylate gives rise to only weakly active analogues (9x). Conformational studies (NMR, X-ray crystallography) of the 2-pyrazinylcarboxamidobenzoates indicate that the preferred conformation exhibits a trans-amide bond and an internal hydrogen bond between the quinoxaline N1 and HN amide which locks the torsional angle between C2 and CO in the s-trans conformation. N-Methylation (9y) results in loss of activity. Studies indicate that there is now a cis-amide bond present which redirects the carboxylate toward the pharmacophoric gem-dimethyl groups. The distance between the gem-dimethyl group and the terminal carboxylate appears to be too short to activate the retinoid receptor. N-Methylation in the beta-ionylideneacetamidobenzoate series (10c) also results in the formation of a cis-amide bond and loss of activity.