2-(quinolin-8-yloxy)benzaldehyde | 893752-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(quinolin-8-yloxy)benzaldehyde
• 英文别名: 2-Quinolin-8-yloxybenzaldehyde
• CAS: 893752-62-0
• 化学式: C₁₆H₁₁NO₂
• mdl: MFCD07365227
• 分子量: 249.269
• InChiKey: SYCCNNJDYQDPAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(quinolin-8-yloxy)benzaldehyde 在 叔丁基过氧化氢 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 24.0h， 以53%的产率得到7H-<1>benzopyrano<3,2-h>quinolin-7-one
  参考文献：
  名称：

  无金属的氧化偶联：通过四丁基溴化铵作为促进剂，在水性介质中直接环合2-芳氧基苯甲醛制得的蒽酮

  摘要：

  AbstractA metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron‐donating and electron‐withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.magnified image

  DOI：

  10.1002/adsc.201300488
• 作为产物：
  描述：

  8-羟基喹啉 、 2-氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 以45%的产率得到2-(quinolin-8-yloxy)benzaldehyde
  参考文献：
  名称：

  无金属的氧化偶联：通过四丁基溴化铵作为促进剂，在水性介质中直接环合2-芳氧基苯甲醛制得的蒽酮

  摘要：

  AbstractA metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron‐donating and electron‐withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.magnified image

  DOI：

  10.1002/adsc.201300488

文献信息

• Metal-Free Oxidative Coupling: Xanthone Formation<i>via</i>Direct Annulation of 2-Aryloxybenzaldehyde using Tetrabutylammonium Bromide as a Promoter in Aqueous Medium
  作者：Honghua Rao、Xinyi Ma、Qianzi Liu、Zhongfeng Li、Shengli Cao、Chao-Jun Li

  DOI：10.1002/adsc.201300488

  日期：2013.8.12

  AbstractA metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron‐donating and electron‐withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.magnified image