2-(phenanthren-9-yloxy)pyridine | 1246204-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-(phenanthren-9-yloxy)pyridine
• CAS: 1246204-88-5
• 化学式: C₁₉H₁₃NO
• 分子量: 271.318
• InChiKey: OZPZESXIJGAUAC-UHFFFAOYSA-N

物化性质

• 沸点：
  472.5±18.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-甲酸苯基三氟硼酸钾 、 2-(phenanthren-9-yloxy)pyridine 在 水 、 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13 mg的产率得到4-(10-(pyridin-2-yloxy)phenanthren-9-yl)benzaldehyde
  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
• 作为产物：
  描述：

  2-碘吡啶 、 9-羟基菲 在 铜 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以40%的产率得到2-(phenanthren-9-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。
• Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)–O Bonds with a Traceless Activation Strategy
  作者：Fei Fan、Jinghua Tang、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.joc.8b02104

  日期：2018.11.2

  We report here the chromium-catalyzed regioselective Kumada arylative cross-coupling of C(aryl)-O bonds at ambient temperature. By using a simple and low-cost chromium(II) chloride salt as a precatalyst, accompanied by a 2-pyridyl ligation, the catalytic cleavage and arylative coupling of C(aryl)-O bonds were achieved with a traceless activation strategy, overcoming the regioselectivity obstacle when several C-O bonds coexist in the Kumada coupling system.