2-(4'-methoxybiphenyl-2-yloxy)pyridine | 1246204-76-1

• 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-(4'-methoxybiphenyl-2-yloxy)pyridine
• 英文别名: 2-{(4'-methoxy-[1,1'-biphenyl]-2-yl)oxy}pyridine；2-[2-(4-Methoxyphenyl)phenoxy]pyridine；2-[2-(4-methoxyphenyl)phenoxy]pyridine
• CAS: 1246204-76-1
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: DDBPLHYACZPDTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-methoxybiphenyl-2-yloxy)pyridine 在 三氟甲烷磺酸甲酯 、 甲醇 、 sodium 作用下， 以 甲苯 为溶剂， 反应 2.25h， 以81%的产率得到2-(4-甲氧基苯基)苯酚
  参考文献：
  名称：

  Ruthenium-Catalyzed C–H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles

  摘要：

  Ruthenium-catalyzed direct arylations of phenols bearing removable directing groups were accomplished through carboxylate assistance via six-membered ruthenacycles as key intermediates.

  DOI：

  10.1021/ol3000876
• 作为产物：
  描述：

  2-苯氧基吡啶 、 (4-甲氧基苯基)三氟硼酸钾 在 palladium diacetate 、 二甲基亚砜 、 silver carbonate 、 对苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以8.3 mg的产率得到2-(4'-methoxybiphenyl-2-yloxy)pyridine
  参考文献：
  名称：

  Palladium(II)-Catalyzed Ortho Arylation of 2-Phenoxypyridines with Potassium Aryltrifluoroborates via C−H Functionalization

  摘要：

  An efficient synthesis of ortho-arylated 2-phenoxypyridines catalyzed by palladium acetate is described. Treatment of 2-phenoxypyridines with two and a half equivalents of potassium aryltrifluoroborate and 10 mol % of Pd(OAc)(2) in the presence of two equivalents of Ag(2)CO(3), one equivalent of p-benzoquinone (BQ), and four equivalents of DMSO with (or without) H(2)O at 130-140 degrees C for 48 h in dried CH(2)Cl(2) gave the ortho-arylated 2-phenoxypyridines in modest to excellent yields. p-Benzoquinone is found to be an important ligand and co-oxidant for the transmetalation reductive elimination step in the catalytic reaction. The investigation of kinetic isotope effect (k(H)/k(D)) is determined to be 5.25, which indicates that C H bond cleavage occurs in the rate-determining step. One of the arylated compounds, 2-(4'-nitrobiphenyl-2-yloxy)pyridine, was treated with methyl trifluoromethanesulfonate and subsequently sodium methoxide to give the 2-(4-nitrophenyl)phenol in 79% yield, demonstrating that pyridine is a removable directing group.

  DOI：

  10.1021/om100494p

文献信息

• Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C–O Bonds
  作者：Xiaoqin Zeng、Yuxuan Zhang、Zhengli Liu、Shasha Geng、Yun He、Zhang Feng

  DOI：10.1021/acs.orglett.0c00679

  日期：2020.4.17

  Herein, we report the iron-catalyzed borylation of aryl ethers and aryl amines via cleavage of C–O and C–N bonds. This protocol does not require the use of Grignard reagents and displays a broad substrate scope, which allows the late-stage borylation. It also provides facile access to multisubstituted arenes through C–H functionalization using 2-pyridyloxy as the directing group.

  在本文中，我们报道了通过C–O和C–N键的裂解，铁催化的芳基醚和芳基胺的硼化反应。该方案不需要使用格氏试剂，并且显示了较宽的底物范围，可以进行后期硼化。它也可以通过使用2-吡啶氧基作为导向基团的C–H官能化轻松访问多取代的芳烃。
• Palladium(II)-Catalyzed <i>Ortho</i> Arylation of 2-Phenoxypyridines with Potassium Aryltrifluoroborates via C−H Functionalization
  作者：Jean-Ho Chu、Pi-Shan Lin、Ming-Jung Wu

  DOI：10.1021/om100494p

  日期：2010.9.27

  An efficient synthesis of ortho-arylated 2-phenoxypyridines catalyzed by palladium acetate is described. Treatment of 2-phenoxypyridines with two and a half equivalents of potassium aryltrifluoroborate and 10 mol % of Pd(OAc)(2) in the presence of two equivalents of Ag(2)CO(3), one equivalent of p-benzoquinone (BQ), and four equivalents of DMSO with (or without) H(2)O at 130-140 degrees C for 48 h in dried CH(2)Cl(2) gave the ortho-arylated 2-phenoxypyridines in modest to excellent yields. p-Benzoquinone is found to be an important ligand and co-oxidant for the transmetalation reductive elimination step in the catalytic reaction. The investigation of kinetic isotope effect (k(H)/k(D)) is determined to be 5.25, which indicates that C H bond cleavage occurs in the rate-determining step. One of the arylated compounds, 2-(4'-nitrobiphenyl-2-yloxy)pyridine, was treated with methyl trifluoromethanesulfonate and subsequently sodium methoxide to give the 2-(4-nitrophenyl)phenol in 79% yield, demonstrating that pyridine is a removable directing group.
• Ruthenium-Catalyzed C–H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles
  作者：Lutz Ackermann、Emelyne Diers、Atul Manvar

  DOI：10.1021/ol3000876

  日期：2012.2.17

  Ruthenium-catalyzed direct arylations of phenols bearing removable directing groups were accomplished through carboxylate assistance via six-membered ruthenacycles as key intermediates.