1-(2,6-dichloro-4-phenylethynylpyridin-3-yl)ethanone | 1443680-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,6-dichloro-4-phenylethynylpyridin-3-yl)ethanone
• 英文别名: 1-[2,6-Dichloro-4-(2-phenylethynyl)pyridin-3-yl]ethanone
• CAS: 1443680-01-0
• 化学式: C₁₅H₉Cl₂NO
• 分子量: 290.149
• InChiKey: USENZXFDLSLKGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,6-dichloro-4-phenylethynylpyridin-3-yl)ethanone 、 丙炔酸甲酯 在 gold(III) chloride 、 silver hexafluoroantimonate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以57%的产率得到5-benzoyl-1,3-dichloro-8-methylisoquinoline-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Gold-Catalyzed Benzannulation of Electronically Rich/Rich and Deficient/Deficient Oxoalkynes with Alkynes

  摘要：

  Two different strategies have been developed to perform the gold-catalyzed benzannulation of both electron-rich pyridine containing oxoalkynes with electron-rich alkynes as well as electron-deficient pyridine containing oxoalkynes with electron-deficient alkynes. The benzannulation between electron-rich oxoalkynes with electron-rich alkynes proceeds in the presence of highly electron-deficient gold catalysts, whereas using catalytic amount of alcohol benzannulation was performed efficiently between electron-deficient oxoalkynes with electron-deficient alkynes.

  DOI：

  10.1055/s-0032-1318454
• 作为产物：
  描述：

  2,6-dichloro-4-iodonicotinaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 1-(2,6-dichloro-4-phenylethynylpyridin-3-yl)ethanone
  参考文献：
  名称：

  Gold-Catalyzed Benzannulation of Electronically Rich/Rich and Deficient/Deficient Oxoalkynes with Alkynes

  摘要：

  Two different strategies have been developed to perform the gold-catalyzed benzannulation of both electron-rich pyridine containing oxoalkynes with electron-rich alkynes as well as electron-deficient pyridine containing oxoalkynes with electron-deficient alkynes. The benzannulation between electron-rich oxoalkynes with electron-rich alkynes proceeds in the presence of highly electron-deficient gold catalysts, whereas using catalytic amount of alcohol benzannulation was performed efficiently between electron-deficient oxoalkynes with electron-deficient alkynes.

  DOI：

  10.1055/s-0032-1318454