N-(2-(4-(trifluoromethyl)benzoyl)phenyl)acetamide | 120301-10-2

• 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-(2-(4-(trifluoromethyl)benzoyl)phenyl)acetamide
• 英文别名: 2-(Acetylamino)-4'-(trifluoromethyl)benzophenone；N-[2-[4-(trifluoromethyl)benzoyl]phenyl]acetamide
• CAS: 120301-10-2
• 化学式: C₁₆H₁₂F₃NO₂
• 分子量: 307.272
• InChiKey: RJTOQIFOZQEBFM-UHFFFAOYSA-N

物化性质

• 沸点：
  479.1±45.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(4-(trifluoromethyl)benzoyl)phenyl)acetamide 在 盐酸 、 potassium carbonate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 N-(2-(4-(1,1,1-trifluoromethyl)benzoylphenyl))-2-bromoacetamide
  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
• 作为产物：
  描述：

  苯胺 在 叔丁基过氧化氢 、 三氟甲磺酸 、 palladium diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 N-(2-(4-(trifluoromethyl)benzoyl)phenyl)acetamide
  参考文献：
  名称：

  钯催化苯乙醇对乙酰苯胺的氧化CH键酰化反应

  摘要：

  通过在三氟甲磺酸（TfOH）存在下用乙酸钯催化的过氧化氢叔丁基酯（TBHP）作为氧化剂，通过乙酰苯胺与苄醇的酰化反应，开发了一种构建CC键的有效且清洁的方法。酰化反应显示出优异的反应性，并且在最佳条件下可获得高达95％的相应芳基酮收率。

  DOI：

  10.1002/adsc.201100417

文献信息

• Palladium-Catalyzed C-H Bond Acylation of Acetanilides with Benzylic Alcohols under Aqueous Conditions
  作者：Feihua Luo、Jun Yang、Zhengkai Li、Haifeng Xiang、Xiangge Zhou

  DOI：10.1002/ejoc.201500016

  日期：2015.4

  Palladium-catalyzed dehydrogenative coupling reactions between acetanilides and benzylic alcohols under aqueous conditions are reported. A wide range of benzophenone derivatives could be obtained in good to excellent yields up to 98 %. Mechanism studies showed that a bimetallic palladium cyclopalladated complex might be involved in the catalysis.

  报道了在水性条件下钯催化乙酰苯胺和苯甲醇之间的脱氢偶联反应。可以获得多种二苯甲酮衍生物，产率高达 98%。机理研究表明，双金属钯环钯配合物可能参与催化。
• A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines.
  作者：Katsuhiko HINO、Katsuyoshi KAWASHIMA、Makoto OKA、Yasutaka NAGAI、Hitoshi UNO、Jun-ichi MATSUMOTO

  DOI：10.1248/cpb.37.110

  日期：——

  The synthesis of a novel class of antiulcer agents, the substituted 4-phenyl-2-(1-piperazinyl)quinolines, and their pharmacological activities (inhibitory effects on hypothermia induced by reserpine and on gastric ulcers induced by stress or ethanol) are described. These compounds can be classified into three groups (a group predominantly effective on the stress-induced ulcer, one effective on both the stress- and ethanol-induced ulcers, and one selectively effective on the ethanol-induced ulcer), with regard to antiulcer activity. The inhibitory effect on stress-induced ulcer was found to be in close relation to the antagonism of hypothermia. The structure-activity relationships in these compounds are described. Among the compounds, 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline dimaleate (9, AS-2646) showed a potent inhibition of stress-induced ulcer and gastric acid secretion, possively through action on the central nervous system, and it was selected for clinical evaluation.

  描述了一类新型抗溃疡药物的合成，即取代的4-苯基-2-(1-哌嗪基)喹啉，以及它们的药理活性（对由雷沙平引起的低温及由压力或乙醇引起的胃溃疡的抑制作用）。这些化合物可根据抗溃疡活性分为三类（针对压力诱导溃疡具有主导效应的一类、对压力和乙醇诱导的溃疡均有效的一类，以及对乙醇诱导溃疡选择性有效的一类）。在压力诱导的溃疡中，抑制作用与对低温的拮抗作用密切相关。描述了这些化合物的结构-活性关系。在这些化合物中，2-(4-乙基-1-哌嗪基)-4-苯基喹啉二马来酸盐（9，AS-2646）对压力诱导的溃疡和胃酸分泌表现出显著抑制作用，可能通过对中枢神经系统的作用实现，因此被选中进行临床评估。
• Merging Photoredox with Palladium Catalysis: Decarboxylative <i>ortho</i>-Acylation of Acetanilides with α-Oxocarboxylic Acids under Mild Reaction Conditions
  作者：Chao Zhou、Pinhua Li、Xianjin Zhu、Lei Wang

  DOI：10.1021/acs.orglett.5b03192

  日期：2015.12.18

  temperature decarboxylative ortho-acylation of acetanilides with α-oxocarboxylic acids has been developed via a novel Eosin Y with Pd dual catalytic system. This dual catalytic reaction shows a broad substrate scope and good functional group tolerance, and an array of ortho-acylacetanilides can be afforded in high yields under mild conditions.

  通过具有Pd双催化体系的新型曙红Y，开发了一种室温下将乙酰苯胺与α-氧代羧酸进行脱羧邻位酰化的方法。这种双重催化反应显示出较宽的底物范围和良好的官能团耐受性，在温和条件下可以高收率获得一系列邻酰基乙酰苯胺。
• Palladium-Catalyzed ortho-Acylation of Acetanilides with Aldehydes through Direct CH Bond Activation
  作者：Chengliang Li、Lei Wang、Pinhua Li、Wei Zhou

  DOI：10.1002/chem.201101192

  日期：2011.9.5

  Easy access to o‐acyl acetanilides: A new Pd‐catalyzed ortho‐acylation of acetanilides with both aromatic and aliphatic aldehydes has been developed based on a CH activation process. In the presence of tert‐butyl hydroperoxide (TBHP) as the ideal oxidant, this reaction provides an efficient access to ortho‐acyl acetanilides in good yields (see scheme).

  方便地访问 ö酰基乙酰苯胺： -催化的钯的新邻用芳族和脂族醛乙酰苯胺的酰化已经基于一个C已经开发 ħ激活过程。在存在叔丁基过氧化氢（TBHP）作为理想氧化剂的情况下，该反应可高效获得高收率的邻酰基乙酰苯胺（参见方案）。
• Room Temperature Palladium-Catalyzed Decarboxylative <i>ortho</i>-Acylation of Acetanilides with α-Oxocarboxylic Acids
  作者：Ping Fang、Mingzong Li、Haibo Ge

  DOI：10.1021/ja105245f

  日期：2010.9.1

  A novel Pd-catalyzed decarboxylative ortho-acylation of acetanilides with alpha-oxocarboxylic acids is realized at room temperature. This reaction provides efficient access to o-acyl acetanilides under mild conditions.