(3,5-dimethylphenyl)(2-(pyridin-2’-yl)phenyl)methanone | 1401733-33-2

• 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: (3,5-dimethylphenyl)(2-(pyridin-2’-yl)phenyl)methanone
• 英文别名: (3, 5-dimethylphenyl)(2-(pyridin-2-yl)phenyl)methanone；(3,5-dimethylphenyl)(2-(pyridin-2-yl)phenyl)methanone
• CAS: 1401733-33-2
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: ONXGAZODBCFLAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-溴吡啶 在 十二羰基三钌 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 邻二甲苯 为溶剂， 160.0 ℃ 、1.0 MPa 条件下， 反应 22.5h， 生成 (3,5-dimethylphenyl)(2-(pyridin-2’-yl)phenyl)methanone
  参考文献：
  名称：

  Ruthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C–N Bond

  摘要：

  Herein, we report the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines via C(aryl)-N bond cleavage. Without any ligand and base, diaryl ketones can be obtained in moderate to high yields by using Ru-3(CO)(12) as the catalyst and chelation assisted by pyridine. The pyridine ring has a significant effect on both high efficiency and high regioselectivity in the cleavage of the aryl C-N bond in anilines.

  DOI：

  10.1021/acs.orglett.0c00736

文献信息

• Manganese-Catalyzed Direct Nucleophilic C(sp²)H Addition to Aldehydes and Nitriles
  作者：Bingwei Zhou、Yuanyuan Hu、Congyang Wang

  DOI：10.1002/anie.201506187

  日期：2015.11.9

  Herein, a manganese‐catalyzed nucleophilic addition of inert C(sp2)H bonds to aldehydes and nitriles is disclosed by virtue of a dual activation strategy. The reactions feature mild reaction conditions, excellent regio‐ and stereoselectivity, and a wide substrate scope, which includes both aromatic and olefinic CH bonds, as well as a large variety of aldehydes and nitriles. Moreover, mechanistic studies

  本文通过双重活化策略公开了锰催化的惰性C（sp 2）H键与醛和腈的亲核加成反应。该反应具有温和的反应条件，出色的区域选择性和立体选择性以及广泛的底物范围，其中包括芳族和烯烃的CH键以及各种醛和腈。此外，机理研究揭示了可能的催化循环。
• Palladium catalyzed direct ortho C–H acylation of 2-arylpyridines using toluene derivatives as acylation reagents
  作者：Zhipeng Xu、Biao Xiang、Peipei Sun

  DOI：10.1039/c2ra22208f

  日期：——

  A facile ortho-acylation of 2-arylpyridines by a Pd-catalyzed oxidative C–H activation was developed, in which no prefunctionalized toluene derivatives were used as acylation reagents in a tandem reaction to form 2-pyridyldiaryl ketones with moderate yields.

  开发了一种简单的2-芳基吡啶的ortho-酰基化反应，采用Pd催化的氧化C–H活化，其中没有使用预功能化的甲苯衍生物作为酰基化试剂，通过级联反应形成2-吡啶基二芳基酮，产率适中。
• Four Tandem C–H Activations: A Sequential C–C and C–O Bond Making via a Pd-Catalyzed Cross Dehydrogenative Coupling (CDC) Approach
  作者：Srimanta Guin、Saroj Kumar Rout、Arghya Banerjee、Shyamapada Nandi、Bhisma K. Patel

  DOI：10.1021/ol302438z

  日期：2012.10.19

  the ortho C–H bond with respect to a directing group has been accomplished via a Pd(II)-catalyzed cross dehydrogenative coupling approach using alkylbenzene as the synthetic equivalent of an aroyl moiety. The reaction proceeds through sequential C–C and C–O bond making at the expense of four consecutive C–H bond cleavages (three sp3 benzylic C–H’s and one sp2 arene C–H) to selectively install an aroyl

  通过使用烷基苯作为芳酰基基团的合成等价物，通过Pd（II）催化的交叉脱氢偶联方法，在相对于一个导向基团的邻位C-H键上实现了空前的芳基化。反应通过连续的C–C和C–O键进行，以四次连续的C–H键裂解（三个sp 3苄基C–H和一个sp 2芳烃C–H）为代价，从而选择性地在芳烃上安装了芳酰基官能团。包含各种引导基团的底物的近端位点。
• Recyclable Pd(II)complex catalyzed oxidative sp2 CH bond acylation of 2-aryl pyridines with toluene derivatives
  作者：Pullaiah C. Perumgani、Sai Prathima Parvathaneni、Srinivas Keesara、Mohan Rao Mandapati

  DOI：10.1016/j.jorganchem.2016.08.028

  日期：2016.11

  complex C was synthesized and characterized using different spectroscopic techniques. In addition the catalytic efficiency of the Pd (II) complex C was evaluated for ortho-acylation of 2-aryl pyridines with toluene derivatives to form aryl ketones via cross dehydrogenative coupling. In this catalytic process toluene acts as an effective coupling partner upon sp3 CH bond oxidation for sp2 CH bond acylation

  合成了可回收的聚合物锚定的Pd（II）复合物C，并使用不同的光谱技术对其进行了表征。此外，评估了Pd（II）配合物C的催化效率，用于2-芳基吡啶与甲苯衍生物的正酰化反应，通过交叉脱氢偶联形成芳基酮。在该催化过程中，甲苯在水上存在Pd（II）/ TBHP体系的情况下，在sp 3 C H键氧化作用下，作为2-芳基吡啶的sp 2 C H键酰化反应的有效偶联伙伴。此外，催化剂C 具有很高的稳定性，可以很容易地回收和再利用四个周期，而其活性和选择性却没有明显降低。
• Ruthenium-Catalyzed Carbonylative CC Coupling in Water by Directed CH Bond Activation
  作者：Anis Tlili、Johannes Schranck、Jola Pospech、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.201301663

  日期：2013.6.10

  arenes bearing ortho‐directing groups (DG) in the presence of a ruthenium catalyst and aryl iodide is presented. The reaction is general for variously substituted aryl iodides to give ketones in moderate to good yields, and water serves as the solvent. The system is highly selective towards the mono‐carbonylative arylation by ortho CH functionalization. cod=cyclo‐1,5‐octadiene.

  首先，首先要介绍的是在钌催化剂和碘化芳基存在下带有邻位导向基团（DG）的芳烃的标题反应。该反应通常用于各种取代的芳基碘化物，以中等至良好的产率得到酮，并且水用作溶剂。该系统是朝向由单芳基化carbonylative高度选择性的邻位 Ç  ħ官能化。cod =环-1,5-辛二烯。