1-methoxy-8-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline | 1163772-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-methoxy-8-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline
• 英文别名: 1,8-dimethoxy-3-phenyl-1H-pyrano[4,3-b]quinoline
• CAS: 1163772-60-8
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: LNEYNRVRQKHKHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 2-氯-6-甲氧基喹啉-3-甲醛 、 苯乙炔 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以71%的产率得到1-methoxy-8-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline
  参考文献：
  名称：

  Copper-Free Palladium-Catalyzed Sonogashira Coupling−Annulation: Efficient One-Pot Synthesis of Functionalized Pyrano[4,3-b]quinolines from 2-Chloro-3-formylquinolines

  摘要：

  A convenient, one-pot, copper-free, Pd-catalyzed methodology has been described for the synthesis of 1,3-disubstituted pyrano[4,3-b]quinolines from 2-chloro-3-formylquinolines. Formation of annulated products 3 is attributed to the presence of Pd(OAc)(2) and MI. Further, PPh3 in the reaction mixture promotes the cyclization by reducing the reaction time and increasing the yield of cyclized product.

  DOI：

  10.1021/jo900606j

文献信息

• Copper-Free Palladium-Catalyzed Sonogashira Coupling−Annulation: Efficient One-Pot Synthesis of Functionalized Pyrano[4,3-<i>b</i>]quinolines from 2-Chloro-3-formylquinolines
  作者：Atish Chandra、Bhawana Singh、Ranjana S. Khanna、Radhey M. Singh

  DOI：10.1021/jo900606j

  日期：2009.8.7

  A convenient, one-pot, copper-free, Pd-catalyzed methodology has been described for the synthesis of 1,3-disubstituted pyrano[4,3-b]quinolines from 2-chloro-3-formylquinolines. Formation of annulated products 3 is attributed to the presence of Pd(OAc)(2) and MI. Further, PPh3 in the reaction mixture promotes the cyclization by reducing the reaction time and increasing the yield of cyclized product.