1-(4-fluorophenyl)-2-(4-methoxyphenyl)propan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-fluorophenyl)-2-(4-methoxyphenyl)propan-1-one
• 英文别名: 1-(4'-Fluorophenyl)-2-(4'-methoxyphenyl)-1-propanone
• 化学式: C₁₆H₁₅FO₂
• 分子量: 258.292
• InChiKey: PWJLYIDEFMLCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4'-氟苯丙酮 、 对氯甲苯 在 [Pd(dibenzylideneacetone)2] diaminochlorophosphine ligand 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到1-(4-fluorophenyl)-2-(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  二氨基氯膦，用于钯催化的胺和酮的芳基化。

  摘要：

  DOI：

  10.1002/anie.200602222

文献信息

• N-Heterocyclic carbene-palladacyclic complexes: synthesis, characterization and their applications in the C-N coupling and α-arylation of ketones using aryl chlorides
  作者：Feng Liu、Yuan-Yuan Hu、Di Li、Quan Zhou、Jian-Mei Lu

  DOI：10.1016/j.tet.2018.07.052

  日期：2018.9

  a one-pot procedure under mild conditions. The structure of 3a was unambiguously confirmed by X-ray single crystal diffraction and it was an active catalyst in the Buchwald-Hartwig amination and α-arylation of ketones even at very low catalyst loadings (0.01 mol%).

  在温和条件下，通过一锅法成功地获得了N-杂环卡宾-四环复合物3。通过X射线单晶衍射明确证实了3a的结构，即使在极低的催化剂负载量（0.01摩尔％）下，它仍是Buchwald-Hartwig胺化和酮的α-芳基化反应中的活性催化剂。
• Palladium-Catalyzed Mono-α-Arylation of Acetone with Aryl Imidazolylsulfonates
  作者：Lutz Ackermann、Vaibhav P. Mehta

  DOI：10.1002/chem.201201394

  日期：2012.8.13

  Set the ace(tone): A palladium catalyst derived from the bidentate XantPhos ligand and Pd(OAc)2 has enabled broadly applicable mono‐α‐arylations of acetone to be performed with air‐ and moisture‐stable aryl imidazolylsulfonates as most user‐friendly electrophiles (see scheme).

  设定ace（tone）：一种由双齿XantPhos配体和Pd（OAc）2衍生的钯催化剂，使得最广泛使用的丙酮单α-芳基化反应可以与空气和水分稳定的芳基咪唑基磺酸盐一起使用，这是最易于使用的亲电试剂（请参阅方案）。
• N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed α-Arylation of Ketones with Aryl Chlorides
  作者：Li-Xiong Shao、Zheng-Kang Xiao

  DOI：10.1055/s-0031-1289698

  日期：2012.3

  An easily available NHC-Pd(II)-Im (NHC = N-heterocyclic carbene, Im = 1-methylimidazole) complex was found to be an efficient catalyst for the α-arylation reaction between ketones and aryl chlorides. Under the optimal conditions, all reactions proceeded smoothly to give the desired products in good to high yields within hours.

  一种易得的 NHC-Pd(II)-Im 复合物（NHC = N-杂环碳氢化物，Im = 甲基咪唑）被发现是一种高效的催化剂，适用于酮和芳香氯之间的 α-芳基化反应。在最佳条件下，所有反应均顺利进行，所需的产物在数小时内以良好到高的产率得到。
• N-heterocyclic carbene-palladium-imine complex catalyzed α-arylation of ketones with aryl and heteroaryl chlorides under air atmosphere
  作者：Hui-Yang Lu、An Shen、Yong-Qing Li、Yu-Cai Hu、Chen Ni、Yu-Cai Cao

  DOI：10.1016/j.tetlet.2020.152124

  日期：2020.7

  synthesized and unambiguously confirmed by X-ray single crystal diffraction. It was found to be an efficient and air-stable catalyst for the α-arylation of ketones. The reaction could be operated in air without any negative effect. Non-activated aryl and heteroaryl chlorides have been successfully applied in the reaction with only 0.5 mol% catalyst loadings under air atmosphere. Excellent to good product yields

  饱和环骨架单连接的NHC-Pd-亚胺络合物的新结构很容易合成，并通过X射线单晶衍射确定。发现它是用于酮的α-芳基化的有效且空气稳定的催化剂。该反应可以在空气中进行而没有任何负面影响。非活化的芳基氯化物和杂芳基氯化物已成功地用于反应中，在空气气氛下催化剂的负载量仅为0.5摩尔％。提供了优良的产品收率。
• DIALKYL(2-ALKOXY-6-AMINOPHENYL)PHOSPHINE, THE PREPARATION METHOD AND USE THEREOF
  申请人：Ma Shengming

  公开号：US20140309422A1

  公开（公告）日：2014-10-16

  The present invention relates to the compound of dialkyl(2-alkoxy-6-aminophenyl)phosphine and the preparation method thereof and the application in the palladium catalyzed coupling reactions of aryl chloride and ketone. The dialkyl(2-alkoxy-6-aminophenyl)phosphine of the present invention could coordinate with the palladium catalyst to highly selectively activate the inert carbon-chlorine bond, and to catalyze direct arylation reaction in the α-position of ketones to produce corresponding coupling compounds. The preparation method of the present invention is a simple one-step method which produces the air-stable dialkyl(2-alkoxy-6-aminophenyl)phosphine. Compared with the synthetic routes of ligands to be used in the activation of carbon-chlorine bonds in the prior arts, the preparation method of the present invention has the advantages of short route and easy operation.

  本发明涉及二烷基（2-烷氧基-6-氨基苯基）膦化合物及其制备方法，以及在钯催化芳基氯化物和酮的偶联反应中的应用。本发明的二烷基（2-烷氧基-6-氨基苯基）膦化合物能够与钯催化剂配位，高度选择性地活化惰性碳-氯键，并催化酮的α位直接芳基化反应，生成相应的偶联化合物。本发明的制备方法是一种简单的一步法，可制备出稳定于空气中的二烷基（2-烷氧基-6-氨基苯基）膦化合物。与先前用于活化碳-氯键的配体的合成路线相比，本发明的制备方法具有路线短、操作简便的优点。