2-(3-ethoxyphenyl)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-(3-ethoxyphenyl)pyridine
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: LDLCHNKSQKFIHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-ethoxyphenyl)pyridine 在 叔丁基过氧化氢 、 copper(l) iodide 、 1,2-二氯乙烷 作用下， 反应 24.0h， 以73%的产率得到2-(2-chloro-5-ethoxyphenyl)pyridine
  参考文献：
  名称：

  铜催化的芳基直接邻位氯化/氧化：氧化剂的转换，控制产物的多样性

  摘要：

  首次以TBHP为氧化剂，以1,2-二氯乙烷为氯化剂，实现了高区域选择性铜催化芳基吡啶的邻氯氯化反应。相同的反应条件下进行开关从TBHP氧化剂到过氧化苯甲酰效果邻-oxygenation。

  DOI：

  10.1016/j.tetlet.2018.11.071
• 作为产物：
  描述：

  2-溴吡啶 、 3-乙氧基苯硼酸 在 potassium phosphate 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以84%的产率得到2-(3-ethoxyphenyl)pyridine
  参考文献：
  名称：

  Suzuki-Miyaura cross-coupling for efficient synthesis of aryl-substituted N-heteroarenes catalyzed by recyclable N-phenylpiperazine-Palladium(II) complex

  摘要：

  Polystyrene supported N-phenylpiperazine-Pd(II) complex D was synthesized and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electronmicroscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and thermal analysis (TG-DTA). This heterogeneous Pd(II) complex showed high catalytic efficiency for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides, aryl chlorides to give the corresponding 2-arylpyridines and heteroarenes. The coupled products were formed in excellent yields at low catalyst loadings under mild reaction conditions. Further, this heterogeneous catalyst showed excellent recyclability and reused for four cycles with no significant decrease in its activity. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2018.03.006

文献信息

• Polystyrene-supported Pd(II) complex-catalysed carboacylation of 2-arylpyridines with alcohols via C─H bond activation under solvent-free conditions
  作者：Pullaiah C. Perumgani、Sai Prathima Parvathaneni、Srinivas Keesara、Mohan Rao Mandapati

  DOI：10.1002/aoc.3581

  日期：2017.3

  was used as an efficient catalyst for the synthesis of aromatic ketones via ortho‐acylation of sp2 C─H bonds of 2‐arylpyridines with alcohols as effective coupling partners. The alcohols were oxidized with tert‐butyl hydroperoxide to their corresponding aldehydes in situ and efficiently coupled with 2‐arylpyridines to form aryl ketones under solvent‐free conditions. Furthermore, catalyst C could be easily

  聚苯乙烯支撑的N，N-二甲基乙二胺Pd（II）配合物C被用作通过芳基吡啶2-芳基吡啶的sp 2 C-H键与醇作为邻位酰化反应有效合成芳族酮的有效催化剂。醇用氢过氧化叔丁基原位氧化为相应的醛，并在无溶剂的条件下与2-芳基吡啶有效偶联形成芳基酮。此外，可以通过简单的过滤容易地回收催化剂C，并在不显着降低活性的情况下重复使用五个循环。
• 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。
• Polystyrene supported Dichloro-(8-aminoquinoline)-Palladium(II) complex catalyzed C H bond activation for ortho-acylation of 2-aryl pyridines
  作者：C. Pullaiah Perumgani、Sai Prathima Parvathaneni、Balaswamy Kodicherla、Srinivas Keesara、Mohan Rao Mandapati

  DOI：10.1016/j.ica.2016.10.014

  日期：2017.1

  Polystyrene-supported Dichloro-(8-aminoquinoline)-Pd(II) complex C was synthesized and its catalytic efficiency was evaluated for ortho-acylation of 2-aryl pyridines with alcohols to form aryl ketones via cross dehydrogenative coupling. In addition in the presence of Pd(II) complex, toluene derivatives were also employed as an effective coupling partner for synthesis of aromatic ketones. Furthermore, this catalyst was highly stable and could be easily recovered by simple filtration and reused for four cycles with no significant decrease in its activity and selectivity. (C) 2016 Elsevier B.V. All rights reserved.
• Pd(II) catalyzed regioselective ortho arylation of 2-arylpyridines, 1-phenyl-1H-pyrazoles, and N-pyridinylcarbazoles with diaryliodonium salts
  作者：M. V. Niladri Raju、G. Manohar Reddy、B. Jaganmohan Reddy、V. Jayathirtha Rao、Sai Prathima Parvathaneni

  DOI：10.1007/s00706-022-02990-0

  日期：2022.12