N-(9-oxo-9H-xanthen-2-yl)acetamide | 861522-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(9-oxo-9H-xanthen-2-yl)acetamide
• 英文别名: 2-acetylamino-9H-xanthen-9-one；2-acetylamino-xanthen-9-one；2-Acetylamino-xanthen-9-on；N-(9-oxoxanthen-2-yl)acetamide
• CAS: 861522-98-7
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: DRMVPANRNUNPTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-(2-formylphenoxy)phenyl)acetamide 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85%的产率得到N-(9-oxo-9H-xanthen-2-yl)acetamide
  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

• Rhodium-Catalyzed Xanthone Formation from 2-Aryloxybenzaldehydes via Cross-Dehydrogenative Coupling (CDC)
  作者：Ping Wang、Honghua Rao、Ruimao Hua、Chao-Jun Li

  DOI：10.1021/ol203381q

  日期：2012.2.3

  A concise and straightforward strategy to construct a xanthone skeleton via an intramolecular cross-dehydrogenative coupling (CDC) of 2-aryloxybenzaldehydes has been developed. The reaction proceeded smoothly without any need of preactivation of the aldehyde group. It can tolerate various functional groups and provides an applicable protocol to construct a wide range of xanthone derivatives.
• 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