(2-Amino-phenyl)-(4-trifluoromethyl-phenyl)-methanone | 790-10-3

• 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-Amino-phenyl)-(4-trifluoromethyl-phenyl)-methanone
• 英文别名: 2-amino-4'-(trifluoromethyl)benzophenone；2-[4-(Trifluoromethyl)benzoyl]aniline；(2-aminophenyl)-[4-(trifluoromethyl)phenyl]methanone
• CAS: 790-10-3
• 化学式: C₁₄H₁₀F₃NO
• 分子量: 265.235
• InChiKey: WJDPHVJEFVAKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Amino-phenyl)-(4-trifluoromethyl-phenyl)-methanone 在 potassium hydroxide 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.54h， 生成 4-[5-(4-chlorophenyl)-3-{2-oxo-4-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinolin-3-yl}-4,5-dihydro-1H-pyrazol-1-yl]-4-oxobutanoic acid
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r
• 作为产物：
  描述：

  N-(2-(4-(trifluoromethyl)benzoyl)phenyl)acetamide 在 盐酸 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以90%的产率得到(2-Amino-phenyl)-(4-trifluoromethyl-phenyl)-methanone
  参考文献：
  名称：

  Carbonyl group coordination preferences in square-planar NiII and PdII complexes of pentadentate ligands by electron-withdrawing/donating substituents

  摘要：

  A series of chirally switchable Ni-II and Pd-II complexes were synthesized and fully characterized by X-ray crystallography and additionally by NMR. It was found that control of the stereochemical preference between (S*,S*) and (S*,R*) diastereomers by substituent modification of the ligand sidearms was possible in the process of crystallization with the preferred coordination of the sidearms generally consistent with expectations based on the electron-donating or -withdrawing properties of the sidearm substituent groups. There were however, quite interesting and unanticipated exceptions counter to chemical intuition and it seems that only for complexes with ortho substituents are strong preferences for the coordination manner necessarily displayed in the solid state based on the electron-withdrawing or -donating properties of the substituents. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.04.029

文献信息

• One-Pot Synthesis of Spirocyclopenta[<i>a</i>]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel–Crafts-Type Cyclization
  作者：Quanzhe Li、Jiaxin Liu、Yin Wei、Min Shi

  DOI：10.1021/acs.joc.9b03126

  日期：2020.2.21

  A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible

  通过碘引发的级联环扩展和炔丙醇系链的亚烷基亚环丁烷在温和条件下的分子内Friedel-Crafts型环化，已开发出一种快速合成螺环戊五烯[a]茚衍生物的有效方法。 。该级联过程可以以克为单位轻松进行。在一系列氘标记和对照实验的基础上，已经提出了合理的反应机理。
• Synthesis of trifluoromethyl substituted nucleophilic glycine equivalents and the investigation of their potential for the preparation of α-amino acids
  作者：Mackenzie Bergagnini-Kolev、Mitchell Howe、Emily Burgess、Payton Wright、Samantha Hamburger、Zhennan Zhong、Shawna B. Ellis、Trevor K. Ellis

  DOI：10.1016/j.tet.2020.131741

  日期：2021.1

  of the complexes under phase transfer catalyzed alkylations with hydroxide bases, as well as the DBU catalyzed Michael Additions of optically active 3′-substituted-2-oxazoladinone amides of unsaturated carboxylic acids. It was found that the trifluoromethyl containing nucleophilic glycine equivalents were more reactive than their non-trifluoromethyl analogues in both reaction types. Therefore, the application

  将介绍几种Ni（II）配合的甘氨酸Schiff碱的合成制备方法，以及对其反应性和实用性的研究。这些研究的关键是在稳定由甘氨酸组分衍生的烯醇化物的共轭体系框架内引入吸电子三氟甲基。在相转移催化的与氢氧化物碱的烷基化反应下，以及在不饱和羧酸的旋光性3'-取代-2-恶唑烷酮酰胺的DBU催化的迈克尔加成反应下，对每种络合物的反应性进行了评估。发现在两种反应类型中，含三氟甲基的亲核甘氨酸当量比其非三氟甲基类似物更具反应性。因此，
• Pd-Catalyzed Regiodivergent Synthesis of Diverse Oxindoles Enabled by the Versatile Heck Reaction of Carbamoyl Chlorides
  作者：Xianqing Wu、Zaiquan Tang、Chengxi Zhang、Chenchen Wang、Licheng Wu、Jingping Qu、Yifeng Chen

  DOI：10.1021/acs.orglett.0c01197

  日期：2020.5.15

  oxindole synthesis bearing an all-carbon quaternary center, enabled by Pd-catalyzed intramolecular cyclization followed by multiple intermolecular Heck reactions of both easily accessible alkene-tethered carbamoyl chlorides and olefins. This protocol obviates the use of prefunctionalized olefinic reagents, exhibits excellent functional group tolerance, and features fascinating reactive versatility.

  我们在这里报告了一个杂杂的吲哚合成，该化合物带有一个全碳四元中心，通过钯催化的分子内环化作用以及随后的多个分子间Heck反应，可轻松进行烯烃系的氨基甲酰氯和烯烃的多分子Heck反应。该方案避免了使用预官能化的烯烃试剂，具有出色的官能团耐受性，并具有令人着迷的反应多功能性。
• Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O₂: a facile protocol to selectively synthesize 2- and 3-vinylindoles
  作者：Bo Cao、Marwan Simaan、Ilan Marek、Yin Wei、Min Shi

  DOI：10.1039/c6cc08731k

  日期：——

  A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as terminal oxidant through [small beta]-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to...

  公开了一种新的钯催化的苯胺系链的亚烷基环丙烷的氧化钯的环化反应，该分子环氧化反应是利用分子氧作为末端氧化剂，通过β-碳的氨基缩合中间体的小量消除。该反应为...提供了有效的途径。
• Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
  作者：Rehanguli Ruzi、Junyang Ma、Xiang‐Ai Yuan、Wenliang Wang、Shanshan Wang、Muliang Zhang、Jie Dai、Jin Xie、Chengjian Zhu

  DOI：10.1002/chem.201903816

  日期：2019.10

  phosphoranyl radical chemistry allows for precise cleavage of a stronger C-O bond and formation of a weaker C-C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral

  已经实现了前所未有的芳香族羧酸脱氧芳基化反应，从而可以构建增强的不对称二芳基酮库。协同的光氧化还原催化作用和磷烷基自由基化学反应可在温和的反应条件下，通过1,5-芳基迁移，精确裂解更强的CO键并形成较弱的CC键。此新协议独立于底物氧化还原电势，电子和取代基效应。在氧化还原中性条件下，它提供了60种合成通用的邻氨基和邻羟基二芳基酮的通用且有希望的途径。此外，以令人满意的产率，它也为全合成喹诺酮生物碱，（±）-yaequinolone A2和viridicatin衍生物提供了一条简洁的途径。