N-(2,6-dimethylphenyl)pyridin-3-amine | 1368018-41-0

• 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: N-(2,6-dimethylphenyl)pyridin-3-amine
• 英文别名: 3-Pyridyl 2,6-Dimethylanilin
• CAS: 1368018-41-0
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: AWNNCSGQVZYNEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯吡啶 、 2,6-二甲基苯胺 在 [Pd(IPr*)(acac)Cl] 、 lithium hexamethyldisilazane 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以79%的产率得到N-(2,6-dimethylphenyl)pyridin-3-amine
  参考文献：
  名称：

  [Pd（IPr *）（acac）Cl]：易于合成的大分子碳氮键形成前催化剂

  摘要：

  [钯（IPR *）（ACAC）CL]的一个非常简单的合成已经从市售的Pd（ACAC）开发2和容易制备的IPr *·HCl的（ACAC =乙酰，知识产权* = Ñ，Ñ双（ 2,6-双（二苯甲基）-4-甲基苯基）咪唑-2-亚烷基）。已经探索了所得的复合物[Pd（IPr *）（acac）Cl]（1）作为布赫瓦尔德-哈特维格芳基化偶联的高活性Pd II预催化剂的反应性。已经成功筛选出了两种偶合伙伴均具有不同电子和空间要求的基板。还通过使用芳基杂二卤化物来探索反应的化学选择性。

  DOI：

  10.1021/om300205c

文献信息

• Flexible Steric Bulky Bis(Imino)acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in Buchwald–Hartwig Amination in Air
  作者：Xiao-Bing Lan、Yinwu Li、Yan-Fang Li、Dong-Sheng Shen、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1021/acs.joc.6b02867

  日期：2017.3.17

  well-defined palladium complexes were found to be excellent precatalysts for Buchwald–Hartwig amination of aryl chlorides with amines in air. The electronic effect of the Pd-PEPPSI complexes and the effect of ancillary pyridine ligands were evaluated, among which complex C3 exhibited the most efficiency. It was demonstrated that the cross-coupling products were obtained in excellent yields in the presence

  为了实现与柔性空间体积策略温和的反应条件下有效的钯催化的交叉耦合反应，一系列的Pd-PEPPSI的（PEPPSI：吡啶增强预催化剂制备，稳定化，和起始）络合物C1 - C6被合成和表征，其中不对称的柔性空间本体被引入到萘基骨架的N-芳基上。这些良好定义的钯络合物是在空气中用胺进行布赫瓦尔德-哈特维格胺化芳基氯化物的极好预催化剂。评估了Pd-PEPPSI配合物的电子效应和辅助吡啶配体的效应，其中配合物C3表现出最高的效率。结果表明，在钯含量为0.5-0.1 mol％的情况下，以优异的产率获得了交叉偶联产物。各种芳基氯化物和杂芳基氯化物以及各种胺均相容。芳基氯的氧化加成被证明是催化循环中决定速率的步骤。可以通过将供电子基团引入Pd-PEPPSI配合物中来增强催化活性。这种类型的Pd-PEPPSI预催化剂显示出迄今为止最具挑战性的C–N交叉偶联反应的效率，该反应不需要无水和惰性气氛保护，表明灵活
• Hypervalent Iodine(III) in Direct Oxidative Amination of Arenes with Heteroaromatic Amines
  作者：Srimanta Manna、Polina O. Serebrennikova、Irina A. Utepova、Andrey P. Antonchick、Oleg N. Chupakhin

  DOI：10.1021/acs.orglett.5b02320

  日期：2015.9.18

  coupling of electron-rich arenes with amino derivatives of electron-deficient heterocycles providing rapid access to scaffolds of bioactive compounds and is based on the application of the hypervalent iodine(III) reagent as an oxidant. Regioselective functionalization of C–H bonds of arenes by the formation of C–N bonds under organocatalytic conditions was demonstrated.

  已经开发了在无金属条件下胺化简单的非官能化芳烃的新颖，温和且实用的方法。该方法允许将富电子芳烃与缺电子杂环的氨基衍生物偶联，从而快速进入生物活性化合物的支架，并且基于高价碘（III）试剂作为氧化剂的应用。证明了在有机催化条件下，通过形成C–N键，芳烃的C–H键具有区域选择性功能。
• Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride
  作者：Danielle C. Samblanet、Joseph A.R. Schmidt

  DOI：10.1016/j.jorganchem.2012.08.027

  日期：2012.12

  While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included. (C) 2012 Elsevier B.V. All rights reserved.