N-(2-(4-fluorobenzoyl)phenyl)acetamide | 842-08-0

• 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-fluorobenzoyl)phenyl)acetamide
• 英文别名: N-[2-(4-fluorobenzoyl)phenyl]acetamide
• CAS: 842-08-0
• 化学式: C₁₅H₁₂FNO₂
• 分子量: 257.264
• InChiKey: RVYCGDKNVAYDLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-(4-fluorobenzoyl)phenyl)acetamide 在 三氟化硼甲醇络合物 、 亚硝酸特丁酯 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到2-(4-fluorobenzoyl)benzenediazonium tetrafluoroborate
  参考文献：
  名称：

  Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions

  摘要：

  The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.

  DOI：

  10.1021/acs.joc.5b00272
• 作为产物：
  描述：

  苯胺 在 叔丁基过氧化氢 、 palladium diacetate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 N-(2-(4-fluorobenzoyl)phenyl)acetamide
  参考文献：
  名称：

  在水性条件下钯催化乙酰苯胺与苄醇的 CH 键酰化

  摘要：

  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。

  DOI：

  10.1002/ejoc.201500016

文献信息

• Room Temperature Palladium-Catalyzed Decarboxylative Acyl/Aroylation using [Fe(III)(EDTA)(η²-O₂)]³⁻as Oxidant at Biological pH
  作者：Sugandha Sharma、Imran A. Khan、Anil K. Saxena

  DOI：10.1002/adsc.201201085

  日期：2013.3.11

  The purple‐coloured iron peroxo complex [Fe(III)EDTA(η2‐O2)]3− as a novel reagent system for Pd‐catalyzed decarboxylative ortho‐acylation of acetanilides with α‐oxocarboxylic acids at room temperature in aqueous media has been realized. This reaction provides an effective access to ortho‐acylacetanilides under mild conditions.

  紫色着色铁过氧络合物的[Fe（III）EDTA（η 2 -O 2）] 3-作为Pd催化脱羧的新型试剂系统邻在含水介质中在室温下用α-氧代羧酸乙酰苯胺的酰化具有被实现。该反应可在温和条件下有效地获得邻酰基乙酰基苯胺。
• Palladium-Catalyzed Oxidative C–H Bond Coupling of Steered Acetanilides and Aldehydes: A Facile Access to <i>ortho</i>-Acylacetanilides
  作者：Yinuo Wu、Baozhu Li、Fei Mao、Xingshu Li、Fuk Yee Kwong

  DOI：10.1021/ol201201a

  日期：2011.6.17

  A palladium-catalyzed oxidative C–H bond functionalization/ortho-acylation of acetanilides using easily accessible aldehyde as the acyl source is described. In the presence of a Pd(TFA)2 catalyst and tert-butylhydroperoxide at 90 °C in general, an array of ortho-acylacetanilides can be afforded in good yields.

  描述了使用容易获得的醛作为酰基源的钯催化的乙苯胺的氧化CH键官能化/邻位酰化反应。通常在90℃下在Pd（TFA）2催化剂和叔丁基氢过氧化物的存在下，可以良好的收率得到一系列邻-酰基乙酰苯胺。
• Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides
  作者：Yinuo Wu、Pui Ying Choy、Fei Mao、Fuk Yee Kwong

  DOI：10.1039/c2cc37352a

  日期：——

  A palladium-catalyzed cascade cross-coupling of acetanilide and toluene for the synthesis of ortho-acylacetanilide is described. Toluene derivatives can act as effective acyl precursors (upon sp(3)-C-H bond oxidation by a Pd/TBHP system) in the oxidative coupling between two C-H bonds. This dehydrogenative Pd-catalyzed ortho-acylation proceeds under mild reaction conditions.

  描述了钯催化的乙酰苯胺和甲苯的级联交叉偶联，用于合成邻酰基乙酰苯胺。甲苯衍生物在两个CH键之间的氧化偶联中可以充当有效的酰基前体（在sp（3）-CH键上通过Pd / TBHP系统氧化）。这种脱氢的Pd催化的邻位酰化反应在温和的反应条件下进行。
• A one-pot process for palladium catalyzed direct C–H acylation of anilines in water using a removable ortho directing group
  作者：Fruzsina Szabó、Dániel Simkó、Zoltán Novák

  DOI：10.1039/c3ra45160g

  日期：——

  A new mild, practical method for the synthesis of aminobenzophenone derivatives through a three step one-pot reaction sequence involving acylation of anilines, palladium catalyzed cross-dehydrogenative coupling of the formed anilides and the hydrolytic cleavage is reported. The full reaction sequence was performed under aqueous conditions.

  报道了一种新的温和，实用的方法，该方法通过三步一锅法反应合成氨基二苯甲酮衍生物，该反应涉及苯胺的酰化，钯催化形成的酸酐的交叉脱氢偶联和水解裂解。完整的反应顺序在水性条件下进行。
• Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones
  作者：Scuhand Basuli、Gedu Satyanarayana

  DOI：10.1002/ejoc.201701250

  日期：2018.2.28

  acetates with aldehydes, was presented. Simple bench-top aldehydes were used as the non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without the directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones via acylation and intramolecular aldol condensation. Significantly, the strategy was extended

  介绍了 [Pd] 催化的碘乙酰苯胺/碘代苯乙酸酯与醛的直接酰化。简单的台式醛用作无毒酰化剂。该协议包括与醛直接偶联，无需激活羰基，也无需导向基团辅助。该策略通过酰化和分子内醛醇缩合应用于多米诺一锅法合成 2-喹啉酮。值得注意的是，该策略已扩展到药物和生物活性化合物的多米诺一锅法合成。