2-(2-ethyl-6-methylphenyl)pyridine

• 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: 2-(2-ethyl-6-methylphenyl)pyridine
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: SYPBDDQAFHVMPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  2-(2-ethyl-6-methylphenyl)pyridine 在 十二羰基三钌 、 norbornene 、 caesium carbonate 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~150.0 ℃ 、101.33 kPa 条件下， 反应 22.5h， 生成 methyl 2-{3-ethyl-2-(pyridin-2-yl)phenyl}acetate
  参考文献：
  名称：

  Sequential Protocol for C(sp³)–H Carboxylation with CO₂: Transition-Metal-Catalyzed Benzylic C–H Silylation and Fluoride-Mediated Carboxylation

  摘要：

  One of the most challenging transformations in current organic chemistry is the catalytic carboxylation of a C(sp(3))-H bond using CO2 gas, an inexpensive and ubiquitous Cl source. A sequential protocol for C(sp(3))-H carboxylation by employing a nitrogen-directed, metal-assisted, C-H activation/catalytic silylation reaction in conjunction with fluoride-mediated carboxylation with CO2 was established. The carboxylation proceeded only at the benzylic C(sp(3))-Si bond, not at the aromatic C(sp(2))-Si, which is advantageous for further manipulations of the products.

  DOI：

  10.1021/ol301431d
• 作为产物：
  描述：

  2-溴吡啶 在 四(三苯基膦)钯 、 palladium diacetate 、 potassium carbonate 作用下， 以 2,2,2-三氟乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-(2-ethyl-6-methylphenyl)pyridine
  参考文献：
  名称：

  钯催化芳烃的电化学C–H烷基化

  摘要：

  钯催化的电化学C–H官能化反应已成为有机合成的诱人工具。该方法为需要苛刻化学氧化剂的常规方法提供了一种替代方法。然而，这种电解需要分裂的电池以避免通过阴极还原使催化剂失活。在这里，我们报告了使用未拆分的电化学池在水中钯催化的芳烃电化学C–H烷基化的第一个例子，从而为将烷基引入芳烃提供了实用的解决方案。

  DOI：

  10.1021/acs.organomet.8b00550

文献信息

• Cobalt-Catalyzed Coupling of Alkyl Grignard Reagent with Benzamide and 2-Phenylpyridine Derivatives through Directed C–H Bond Activation under Air
  作者：Quan Chen、Laurean Ilies、Naohiko Yoshikai、Eiichi Nakamura

  DOI：10.1021/ol2011264

  日期：2011.6.17

  Aromatic carboxamides and 2-phenylpyridine derivatives can be ortho-alkylated with Grignard reagents in the presence of a cobalt catalyst and DMPU as a ligand. The reaction proceeds smoothly at room temperature, using air as the sole oxidant. The dialkylated product is selectively obtained when N-methylcarboxamide is employed as a substrate, whereas N-phenyl- or N-isopropylcarboxamide preferentially

  可以在钴催化剂和DMPU作为配体的情况下，使用Grignard试剂对芳族羧酰胺和2-苯基吡啶衍生物进行邻烷基化。使用空气作为唯一的氧化剂，该反应在室温下平稳进行。当使用N-甲基羧酰胺作为底物时，选择性地获得二烷基化产物，而N-苯基-或N-异丙基羧酰胺优先给出单烷基化产物。
• Rhoda‐Electrocatalyzed C−H Methylation and Paired Electrocatalyzed C−H Ethylation and Propylation
  作者：Krzysztof Kuciński、Hendrik Simon、Lutz Ackermann

  DOI：10.1002/chem.202103837

  日期：2022.1.3

  Rhodium-electrocatalyzed C−H alkylation of N-heteroarenes has been established by using sustainable and eco-friendly electrocatalytic approaches. As a result, several arenes, including biologically relevant purines, diazepam, and amino acids were selectively methylated. Finally, an example of an unprecedented, paired electrolysis approach leading to ethylated and propylated arenes was also discovered

  通过使用可持续且环保的电催化方法，建立了N-杂芳烃的铑电催化C−H 烷基化。结果，几种芳烃，包括生物学相关的嘌呤、地西泮和氨基酸被选择性甲基化。最后，还发现了前所未有的配对电解方法产生乙基化和丙基化芳烃的例子。
• Ru₃(CO)₁₂-Catalyzed Silylation of Benzylic C−H Bonds in Arylpyridines and Arylpyrazoles with Hydrosilanes via C−H Bond Cleavage
  作者：Fumitoshi Kakiuchi、Kazuyuki Tsuchiya、Mitsutaka Matsumoto、Eiichiro Mizushima、Naoto Chatani

  DOI：10.1021/ja047040d

  日期：2004.10.1

  Ruthenium-catalyzed silylation of sp3 C-H bonds at a benzylic position with hydrosilanes gave benzylsilanes. For this silylation reaction, Ru3(CO)12 complex showed high catalytic activity. This silylation proceeded at the methyl C-H bond selectively. For this silylation reaction, pyridyl and pyrazolyl groups, and the imino group in hydrazones, can function as a directing group. Several hydrosilanes

  钌催化在苄基位置的 sp3 CH 键与氢硅烷的硅烷化得到苄基硅烷。对于这种硅烷化反应，Ru3(CO)12 配合物表现出很高的催化活性。这种甲硅烷基化选择性地在甲基 CH 键上进行。对于该甲硅烷基化反应，吡啶基和吡唑基以及腙中的亚氨基可作为导向基团。包括三乙基-、二甲基苯基-、叔丁基二甲基-和三苯基硅烷在内的几种氢硅烷可用作甲硅烷基化试剂。sp2 氮原子与钌配合物的配位对于实现这种硅烷化反应很重要。
• Mild Palladium-Catalyzed C–H Alkylation Using Potassium Alkyltrifluoroborates in Combination with MnF₃
  作者：Sharon R. Neufeldt、Cydney K. Seigerman、Melanie S. Sanford

  DOI：10.1021/ol400888r

  日期：2013.5.3

  A Pd-catalyzed method for ligand-directed C-H alkylation with organoboron reagents is described. The combination of potassium organo-trifluoroborates, MnF3, and a Pd-II catalyst effects pyridine and amide-directed C-H alkylation. These reactions proceed under mild conditions (25-40 degrees C in weakly acidic media), are effective for installing methyl and 1 degrees alkyl groups, and do not require promoters such as benzoquinone.
• Beta-Diketone Ancillary Ligands and Their Metal Complexes Used in Organic Optoelectronic Devices
  申请人：Cheng Chien-Hong

  公开号：US20100270915A1

  公开（公告）日：2010-10-28

  The present invention discloses a phosphor material for organic optoelectronic devices. The phosphor is a complex comprising a metal (Ir or Pt) and an aryl-modified beta-diketone ligand. The complexes of this invention are useful to function as an emitter in the emissive layer of an organic light emitting diode, even as the complex is the main component of this layer.