1,4-phenylenebis(quinolin-3-ylmethanone) | 1396547-94-6

• 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: 1,4-phenylenebis(quinolin-3-ylmethanone)
• 英文别名: [4-(Quinoline-3-carbonyl)phenyl]-quinolin-3-ylmethanone；[4-(quinoline-3-carbonyl)phenyl]-quinolin-3-ylmethanone
• CAS: 1396547-94-6
• 化学式: C₂₆H₁₆N₂O₂
• 分子量: 388.425
• InChiKey: TWAZIMIWIZFSKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-甲酰基苯基)-4-甲基苯磺酰胺 、 p-dipropynoylbenzene 在 三苯基膦 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 0.16h， 以63%的产率得到1,4-phenylenebis(quinolin-3-ylmethanone)
  参考文献：
  名称：

  One-Pot Phosphine-Catalyzed Syntheses of Quinolines

  摘要：

  In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the beta-phosphonium enoate alpha-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.

  DOI：

  10.1021/jo3015825

文献信息

• One-Pot Phosphine-Catalyzed Syntheses of Quinolines
  作者：San Khong、Ohyun Kwon

  DOI：10.1021/jo3015825

  日期：2012.9.21

  In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the beta-phosphonium enoate alpha-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.