3-(4-(trifluoromethyl)phenyl)-1-o-tolylprop-2-yn-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-(trifluoromethyl)phenyl)-1-o-tolylprop-2-yn-1-one
• 英文别名: 1-(o-tolyl)-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-one；1-(2-Methylphenyl)-3-[4-(trifluoromethyl)phenyl]-2-propyne-1-one；1-(2-methylphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one
• 化学式: C₁₇H₁₁F₃O
• 分子量: 288.269
• InChiKey: APLYMDOCTZSISM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(trifluoromethyl)phenyl)-1-o-tolylprop-2-yn-1-one 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以71%的产率得到3-(4-(trifluoromethyl)phenyl)naphthalen-1-ol
  参考文献：
  名称：

  Cu(II)-Catalyzed 6π-Photocyclization of Non-6π Substrates

  摘要：

  This research successfully achieved a Cu(II)-catalyzed 6 pi-photocyclization of non-6 pi substrates. The photo-enolization converts ortho-alkylphenyl alkynl ketones into a triene-type intermediate which undergoes the subsequent 6 pi-photo- facilitates both photoenolization and 6 pi-photocyclization. This research highlighted the tandem reaction strategy and the importance of metal catalysis in photochemistry.

  DOI：

  10.1021/acs.orglett.0c01854
• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 、 邻甲基苯甲酰氯 在 palladium diacetate 、 三乙胺 作用下， 反应 0.17h， 以93%的产率得到3-(4-(trifluoromethyl)phenyl)-1-o-tolylprop-2-yn-1-one
  参考文献：
  名称：

  通过酰氯与末端炔烃的偶联反应，无铜，无配位体和无溶剂的合成炔酮

  摘要：

  据报道，在室温下，广泛的酰基氯与乙酸钯（II）催化的末端炔烃偶合，可得到一种通用，有效的无铜，无配体和无溶剂的炔酮合成方法。

  DOI：

  10.1016/j.tetlet.2006.05.166

文献信息

• Light-enabled, AlCl₃-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes
  作者：Yanbin Zhang、Ruiwen Jin、Guangxing Pan、Hao Guo

  DOI：10.1039/d0cc04636a

  日期：——

  regioselective intramolecular nucleophilic cyclization of alkynes using non-nucleophilic alkyls as the nucleophile is reported. Upon photoexcitation, o-alkylphenyl alkynyl ketones can be transferred into (E)-photoenols. Thus, a nucleophilic methylene is formed from the non-nucleophilic alkyl. An AlCl3 catalyst can stabilize the (E)-photoenol intermediate and facilitate further intramolecular nucleophilic cyclization

  报道了使用非亲核烷基作为亲核试剂的光活化的AlCl 3催化炔烃的区域选择性分子内亲核环化反应。光激发后，邻烷基苯基炔基酮可以转移到（E）-光烯醇中。因此，由非亲核烷基形成亲核亚甲基。AlCl 3催化剂可以稳定（E）-光烯醇中间体，并促进进一步的分子内亲核环化。DFT计算表明，AlCl 3催化的环化是区域选择性的决定步骤。
• Copper-, ligand- and solvent-free synthesis of ynones by coupling acid chlorides with terminal alkynes
  作者：Sanjay S. Palimkar、P. Harish Kumar、Nivrutti R. Jogdand、Thomas Daniel、Rajgopal J. Lahoti、Kumar V. Srinivasan

  DOI：10.1016/j.tetlet.2006.05.166

  日期：2006.7

  A general and efficient copper-, ligand- and solvent-free synthesis of ynones by coupling of a wide range of acid chlorides with terminal alkynes catalyzed by palladium(II) acetate at room temperature is reported.

  据报道，在室温下，广泛的酰基氯与乙酸钯（II）催化的末端炔烃偶合，可得到一种通用，有效的无铜，无配体和无溶剂的炔酮合成方法。
• Simple and Efficient One‐Pot, Three‐Component, Solvent‐Free Synthesis of β‐Enaminones via Sonogashira Coupling–Michael Addition Sequences
  作者：Sanjay S. Palimkar、Vijaykumar S. More、Kumar V. Srinivasan

  DOI：10.1080/00397910801914343

  日期：2008.4

  A simple, efficient, and environmentally friendly one-pot, three-component synthesis of beta-enaminones via Sonogashira coupling-Michael addition sequences under solvent-free conditions has been reported. Also the synthesis of beta-enaminones has been achieved in high yields by the direct reaction of amines with ynones under solvent-free conditions.
• Cu(II)-Catalyzed 6π-Photocyclization of Non-6π Substrates
  作者：Yanbin Zhang、Ruiwen Jin、Wenjie Kang、Hao Guo

  DOI：10.1021/acs.orglett.0c01854

  日期：2020.7.17

  This research successfully achieved a Cu(II)-catalyzed 6 pi-photocyclization of non-6 pi substrates. The photo-enolization converts ortho-alkylphenyl alkynl ketones into a triene-type intermediate which undergoes the subsequent 6 pi-photo- facilitates both photoenolization and 6 pi-photocyclization. This research highlighted the tandem reaction strategy and the importance of metal catalysis in photochemistry.