2-(2,6-dimethylphenyl)-1-phenylethan-1-one | 23592-90-7

• 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: 2-(2,6-dimethylphenyl)-1-phenylethan-1-one
• 英文别名: α-(2,6-dimethylphenyl)acetophenone；2-(2,6-dimethylphenyl)-1-phenylethanone；ω-(2,6-dimethylphenyl)acetophenone；Ethanone, 2-(2,6-dimethylphenyl)-1-phenyl-
• CAS: 23592-90-7
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: ORXWZKKYZBGIAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 苯乙酮 在 C₄₁H₅₀ClN₃Pd 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以96%的产率得到2-(2,6-dimethylphenyl)-1-phenylethan-1-one
  参考文献：
  名称：

  N-杂环卡宾-钯-亚胺络合物在大气气氛下催化酮与芳基和杂芳基氯化物的α-芳基化

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2020.152124

文献信息

• Synthesis of novel (NHC)Pd(acac)Cl complexes (acac=acetylacetonate) and their activity in cross-coupling reactions
  作者：Oscar Navarro、Nicolas Marion、Natalie M. Scott、Juan González、Dino Amoroso、Andrew Bell、Steven P. Nolan

  DOI：10.1016/j.tet.2005.06.081

  日期：2005.10

  The synthesis and characterization of two new complexes (IPr)Pd(acac)2 (1) and (IPr)Pd(acac)Cl (2) (IPr=(N,N'-bis(2,6-diisopropylphenyl)imidazol)-2-ylidene, acac=acetylacetonate) are described. Complex 2 can be prepared in a one-pot protocol in high yield. A study detailing the versatility of 2 to effectively catalyze a series of cross-coupling reactions is discussed.

  两种新配合物（IPr）Pd（acac）2（1）和（IPr）Pd（acac）Cl（2）（IPr =（N，N'-双（2,6-二异丙基苯基）咪唑）的合成和表征描述了-2-亚烷基，acac ＝乙酰丙酮酸酯。配合物2可以一锅法高产率制备。讨论了详细研究2的多功能性以有效催化一系列交叉偶联反应的研究。
• N-Heterocyclic Carbene Adducts of Cyclopalladated Ferrocenylpyridazine: Synthesis, Structural Characterization, and Application in ?-Arylation of Ketones with Aryl Chlorides
  作者：Chen Xu、Hong-Mei Li、Zhi-Qiang Wang、Wei-Jun Fu、Yu-Qing Zhang、Bao-Ming Ji

  DOI：10.1071/ch12035

  日期：——

  3-chloro-6-pyridazinylferrocene 1 and its N-heterocyclic carbene adducts 2–3 were synthesized and characterized by 1H NMR and IR spectroscopy, ESI-MS, and elemental analysis. Additionally, detailed structures of complexes 2–3 have been determined by single-crystal X-ray analysis. Complex 3 exhibited high catalytic activity for α-arylation of ketones with aryl chlorides. Typically, using 1 mol % catalyst in the presence

  一种新的二茂铁基配体3-氯-6- pyridazinylferrocene 1及其ñ -杂环卡宾加合物2 - 3被合成和表征通过1 H NMR和IR光谱，ESI-MS，和元素分析。此外，配合物2 – 3的详细结构已通过单晶X射线分析确定。配合物3对酮与芳基氯的α-芳基化反应显示出高催化活性。典型地，在100℃下在1.5当量的t BuOK作为碱存在下于二恶烷中使用1mol％的催化剂以良好的收率提供了偶联产物。
• Di-<i>tert</i>-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones
  作者：Steven M. Raders、Jessica M. Jones、Jeffrey G. Semmes、Steven P. Kelley、Robin D. Rogers、Kevin H. Shaughnessy

  DOI：10.1002/ejoc.201402474

  日期：2014.11

  palladium(II) acetate provide an efficient catalytic system for the α-arylation of ketones. Aryl bromides were coupled with ketones using 0.25–0.5 mol-% Pd(OAc)2/DTBNpP in toluene at 50 °C, whereas aryl chlorides required a higher catalyst loading (0.5–2.0 mol-%) and a higher temperature (80 °C). Coupling of 2-bromophenol with ketones using the Pd/DTBNpP system provides an efficient route for the synthesis

  二叔丁基新戊基膦 (DTBNpP) 和醋酸钯 (II) 为酮的 α-芳基化提供了有效的催化体系。在 50 °C 的甲苯中使用 0.25–0.5 mol-% Pd(OAc)2/DTBNpP 将芳基溴与酮偶联，而芳基氯需要更高的催化剂负载量 (0.5-2.0 mol-%) 和更高的温度 (80 °C) C）。使用 Pd/DTBNpP 系统将 2-溴苯酚与酮偶联为苯并呋喃的合成提供了有效途径。
• Carbene adduct of cyclopalladated ferrocenylimine catalyzed α-arylation of ketones with aryl chlorides or bromides
  作者：Jinli Zhang、Xueqian Yang、Xiuling Cui、Yangjie Wu

  DOI：10.1016/j.tet.2011.08.036

  日期：2011.11

  Carbene adduct of cyclopalladated ferrocenylimine exhibited highly catalytic activity for the α-arylation of ketones with aryl halides. The corresponding products were obtained in moderate to excellent yields. Such protocol was applied to various ketones and a broad scope of aryl halides including aryl chlorides, bromides as well as unactivated and sterically hindered aryl halides.

  环palpalated二茂铁亚胺的碳烯加合物对酮与芳基卤化物的α-芳基化反应表现出很高的催化活性。以中等至优异的产率获得了相应的产物。该方案适用于各种酮类和广泛范围的芳基卤化物，包括芳基氯化物，溴化物以及未活化和空间受阻的芳基卤化物。
• Palladium-Catalyzed α-Arylation of Arylketones at Low Catalyst Loadings
  作者：Enrico Marelli、Martin Corpet、Sian R. Davies、Steven P. Nolan

  DOI：10.1002/chem.201404900

  日期：2014.12.22

  involves the use of a preformed, bench‐stable Pd–N‐heterocyclic carbene pre‐catalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre‐catalyst was also successfully tested in the synthesis of an industrially relevant

  已经开发出用于芳基酮α-芳基化的一般催化方案。它涉及使用预成型的，板凳稳定的Pd– N杂环卡宾预催化剂作为辅助配体，并允许在非常低的催化剂负载量下偶联各种官能化的偶联伙伴。仔细选择溶剂/碱体系对于获得最佳催化剂性能至关重要。在合成工业上有用的化合物时，也成功地测试了前催化剂。