2'-(4-trifluoromethylbenzyloxy)acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(4-trifluoromethylbenzyloxy)acetophenone
• 英文别名: 1-[2-[[4-(Trifluoromethyl)phenyl]methoxy]phenyl]ethanone
• 化学式: C₁₆H₁₃F₃O₂
• 分子量: 294.273
• InChiKey: GMXUWAFGTZPLBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-(4-trifluoromethylbenzyloxy)acetophenone 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以18%的产率得到
  参考文献：
  名称：

  Tetraalkylammonium-Templated Stereoselective Norrish–Yang Cyclization

  摘要：

  Tetrabutylammonium salts serve as templates for the Norrish-Yang cyclization of 2-benzyloxy-acylbenzenes to give trans-dihydrobenzofuranols in high stereoselectivities. The dual cation-pi interactions between an ammonium with a benzene ring and a carbonyl group play a key role in changing the conformation of the substrate, which was supported by ab initio calculations.

  DOI：

  10.1021/ol4028732
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 1-溴-三氟对二甲苯 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 以51%的产率得到2'-(4-trifluoromethylbenzyloxy)acetophenone
  参考文献：
  名称：

  Tetraalkylammonium-Templated Stereoselective Norrish–Yang Cyclization

  摘要：

  Tetrabutylammonium salts serve as templates for the Norrish-Yang cyclization of 2-benzyloxy-acylbenzenes to give trans-dihydrobenzofuranols in high stereoselectivities. The dual cation-pi interactions between an ammonium with a benzene ring and a carbonyl group play a key role in changing the conformation of the substrate, which was supported by ab initio calculations.

  DOI：

  10.1021/ol4028732

文献信息

• Tetraalkylammonium-Templated Stereoselective Norrish–Yang Cyclization
  作者：Shinji Yamada、Azusa Iwaoka、Yuka Fujita、Seiji Tsuzuki

  DOI：10.1021/ol4028732

  日期：2013.12.6

  Tetrabutylammonium salts serve as templates for the Norrish-Yang cyclization of 2-benzyloxy-acylbenzenes to give trans-dihydrobenzofuranols in high stereoselectivities. The dual cation-pi interactions between an ammonium with a benzene ring and a carbonyl group play a key role in changing the conformation of the substrate, which was supported by ab initio calculations.