3-trifluoromethylxanthone | 889946-39-8

• 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: 3-trifluoromethylxanthone
• 英文别名: 3-trifluoromethyl-9H-xanthen-9-one；3-trifluouromethyl-9H-xanthen-9-one；3-(Trifluoromethyl)-9H-xanthene-9-one；3-(trifluoromethyl)xanthen-9-one
• CAS: 889946-39-8
• 化学式: C₁₄H₇F₃O₂
• 分子量: 264.204
• InChiKey: WPPKFLKLVVHDAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(3-trifluoromethylphenoxy)benzaldehyde 在 叔丁基过氧化氢 、 rhodium(III) chloride 、 三苯基膦 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以50%的产率得到3-trifluoromethylxanthone
  参考文献：
  名称：

  Rhodium-Catalyzed Xanthone Formation from 2-Aryloxybenzaldehydes via Cross-Dehydrogenative Coupling (CDC)

  摘要：

  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.

  DOI：

  10.1021/ol203381q

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.
• Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H cross-dehydrogenative coupling (CDC)
  作者：Hanyang Bao、Xiaojun Hu、Jian Zhang、Yunkui Liu

  DOI：10.1016/j.tet.2019.130533

  日期：2019.10

  A Cu(0)/Selectfluor system-catalyzed intramolecular C-sp2-H/C-sp2-H bond cross-dehydrogenative coupling of 2-aryloxybenzaldehydes is described. A variety of substituted xanthone derivatives are synthesized in moderate to excellent yields. Reaction can also be extended to the synthesis of 9H-thioxanthen-9-one 10,10-dioxide and phenanthridin-6(5H)-ones, respectively. (C) 2019 Elsevier Ltd. All rights reserved.
• 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