2-(2,2-diphenylethyl)-3-methylpyridine | 1370412-49-9

• 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: 2-(2,2-diphenylethyl)-3-methylpyridine
• 英文别名: 2-methyl-1-(2,2-diphenyl)ethylpyridine
• CAS: 1370412-49-9
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: OZPROTLEBJPJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-methyl-2-(phenylethynyl)pyridine 在 十二羰基三钌 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 频哪酮 、 乙醇 为溶剂， 20.0~140.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 2-(2,2-diphenylethyl)-3-methylpyridine
  参考文献：
  名称：

  Ruthenium(0)-Catalyzed sp³ C–H Bond Arylation of Benzylic Amines Using Arylboronates

  摘要：

  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.

  DOI：

  10.1021/ol300627p

文献信息

• Photocatalytic activation of pyridine for addition reactions: an unconventional reaction feature between a photo-induced hole and electron on TiO₂
  作者：Dongge Ma、Yan Yan、Hongwei Ji、Chuncheng Chen、Jincai Zhao

  DOI：10.1039/c5cc07123b

  日期：——

  TiO₂ photocatalysis has the ability to furnish a class of coordinated anti-Markovnikov addition reactions between vinylarenes and pyridines. Such pyridine addition reactions occur through a previously undescribed concerted pathway.

  TiO2光催化具有提供一类协同的反马尔科夫尼科夫加成反应的能力，该反应发生在乙烯芳烃和吡啶之间。这种吡啶加成反应是通过一种先前未描述的协同途径发生的。
• 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.