3-methyl-2-phenethylpyridine | 56826-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-methyl-2-phenethylpyridine
• 英文别名: 3-Methyl-2-(2-phenylethyl)pyridine
• CAS: 56826-32-5
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: RKNGKJOFGOTSCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-2-phenethylpyridine 在 十二羰基三钌 、 氘代叔丁醇 作用下， 反应 24.0h， 生成 2-(1,1-dideutero-2-phenylethyl)-6-deutero-3-methylpyridine
  参考文献：
  名称：

  富电子和贫电子氮原子的选择性Ru（0）催化氘代

  摘要：

  使用t的高选择性Ru 3（CO）12催化氘化方法-以BuOD作为氘源。富电子和贫电子的N-杂芳烃，例如吲哚，氮杂吲哚，脱氮杂嘌呤，苯并咪唑，喹啉，异喹啉和吡啶，在特定位置具有较高的氘选择性；在大多数情况下，氘的掺入量接近理论上可能的值。为了进一步提高氘化程度，可以执行几个反应方案的循环，与已建立的方案相比，使用较少量的氘化剂可得到更高的氘化程度。事实证明，相同的方案原则上可以应用于对放射性标记生物活性分子很重要的tri化反应。

  DOI：

  10.1021/jo300219v
• 作为产物：
  描述：

  3-methyl-2-[(E)-2-phenylethenyl]pyridine 以93%的产率得到
  参考文献：
  名称：

  REIMANN E.; SCHWAETZER I.; ZYMALKOWSKI F., J. LIEBIGS ANN. CHEM. , 1975, NO 6, 1070-1080

  摘要：

  DOI：

文献信息

• Aryl Bromides and Aryl Chlorides for the Direct Arylation of Benzylic Amines Mediated by Ruthenium(II)
  作者：Navid Dastbaravardeh、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1002/ejoc.201300004

  日期：2013.5

  importantly, also the cheaper aryl bromides and aryl chlorides can be applied as aryl sources. Additionally, the method does not require elaborate manipulations in a glove box and can be carried out in simple screw cap vials. Potassium pivalate proved to be beneficial for the transformation with aryl bromides or iodides as aryl source, but was not required for aryl chlorides. In the latter case, the addition

  报道了钌(II)催化的苄胺与芳基卤的 sp3 C-H 键芳基化反应。在本方法中，芳基碘化物以及更重要的是更便宜的芳基溴化物和芳基氯化物可以用作芳基源。此外，该方法不需要在手套箱中进行复杂的操作，并且可以在简单的螺旋盖小瓶中进行。新戊酸钾被证明有利于芳基溴或碘化物作为芳基源的转化，但对于芳基氯则不需要。在后一种情况下，PPh3 的添加导致了高转化率。3-甲基和3-苯基吡啶被确定为定向基团，3-位的取代基代表了高转化率的关键结构特征。引导基团可以在转化后裂解，从而获得二芳基甲基胺。进行了机理研究，并与相关转化的机理报告进行了严格的比较。
• Copper-catalyzed cross-coupling of aryl-, primary alkyl-, and secondary alkylboranes with heteroaryl bromides
  作者：Allison M. Bergmann、Adam M. Oldham、Wei You、M. Kevin Brown

  DOI：10.1039/c8cc03145b

  日期：——

  A method for the Cu-catalyzed cross-coupling of both aryl and alkylboranes with aryl bromides is described. The method employs an inexpensive Cu-catalyst and functions for a variety of heterocyclic as well as electron deficient aryl bromides. In addition, aryl iodides of varying substitution patterns and electronic properties work well.

  描述了一种用于Cu催化的芳基和烷基硼烷与芳基溴化物的交叉偶联的方法。该方法使用廉价的Cu催化剂，并且对多种杂环以及电子不足的芳基溴化物起作用。另外，具有不同取代模式和电子性质的芳基碘化物效果很好。
• A New Route to <i>E</i> ‐Stilbenes through the Transition‐Metal‐Free KO <i>t</i> Bu/DMF‐Promoted Direct Coupling of Alcohols with Phenyl Acetonitriles
  作者：Xiaoping Liu、Jean‐Marc Sotiropoulos、Marc Taillefer

  DOI：10.1002/ejoc.202200631

  日期：2022.7.14

  A new route to E-Stilbenes, based on the transition metal free, KOtBu/DMF promoted activation and direct coupling of alcohols with phenyl acetonitriles, is reported. A variation allowing the selective synthesis of N-Heteroarenes and a mechanism proceeding via the activation of alcohols under alkyl formate intermediates are also reported.

  报道了一种基于不含过渡金属、KO t Bu/DMF 的E-二苯乙烯的新途径，它促进了醇与苯基乙腈的活化和直接偶联。还报道了一种允许选择性合成 N-杂芳烃的变化以及通过在甲酸烷基酯中间体下活化醇进行的机制。
• Mechanistic Investigations and Substrate Scope Evaluation of Ruthenium-Catalyzed Direct sp³ Arylation of Benzylic Positions Directed by 3-Substituted Pyridines
  作者：Navid Dastbaravardeh、Karl Kirchner、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/jo302547q

  日期：2013.1.18

  A highly efficient direct arylation process of benzylic amines with arylboronates was developed that employs Ru catalysis. The arylation takes place with greatest efficiency at the benzylic sp(3) carbon. If the distance to the activating aryl ring is increased, arylation is still possible but the yield drops significantly. Efficiency of the CH activation was found to be significantly increased by use of 3-substituted pyridines as directing groups, which can be removed after the transformation in high yield. Calculation of the energy profile of different rotamers of the substrate revealed that presence of a substituent in the 3-position favors a conformation with the CH2 group adopting a position in closer proximity to the directing group and facilitating C-H insertion. This operationally simple reaction can be carried out in argon atmosphere as well as in air and under neutral reaction conditions, displaying a remarkable functional group tolerance. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.
• Ruthenium(0)-Catalyzed sp³ C–H Bond Arylation of Benzylic Amines Using Arylboronates
  作者：Navid Dastbaravardeh、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/ol300627p

  日期：2012.4.6

  A Ru-catalyzed direct arylation of benzylic sp(3) carbons of acyclic amines with arylboronates is reported. This highly regioselective and efficient transformation can be performed with various combinations of N-(2-pyridyl) substituted benzylamines and arylboronates. Substitution of the pyridine directing group in the 3-position proved to be crucial in order to achieve high arylation yields. Furthermore, the pyridine directing group can be removed in high yields via a two-step protocol.