4-(3-(pyridin-2-yloxy)naphthalen-2-yl)benzaldehyde | 1246204-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(3-(pyridin-2-yloxy)naphthalen-2-yl)benzaldehyde
• CAS: 1246204-80-7
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: GHZQGIOPUYTCBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲酸苯基三氟硼酸钾 、 2-(萘-2-酰氧基)吡啶 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9.4 mg的产率得到4-(3-(pyridin-2-yloxy)naphthalen-2-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