(2Z)-4-(pentamethylphenyl)-4-phenyl-3-buten-2-one | 267901-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z)-4-(pentamethylphenyl)-4-phenyl-3-buten-2-one
• 英文别名: (Z)-4-(pentamethylphenyl)-4-phenylbut-3-en-2-one；(Z)-4-pentamethylphenyl-4-phenyl-3-buten-2-one；(Z)-4-(2,3,4,5,6-pentamethylphenyl)-4-phenylbut-3-en-2-one
• CAS: 267901-56-4
• 化学式: C₂₁H₂₄O
• 分子量: 292.421
• InChiKey: ACXINAXQTHKJAO-NDENLUEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z)-4-(pentamethylphenyl)-4-phenyl-3-buten-2-one 在 氟磺酸 作用下， 生成 2-hydroxy-4-pentamethylphenyl-4-phenylbut-3-en-2-ylium
  参考文献：
  名称：

  Alkenylation of arylamines and N-arylacetamides with acetylene compounds in superacids

  摘要：

  Vinyl type cations generated in superacid HSO3F by the protonation of the triple bond of acetylene compounds efficiently react with arylammonium ions and N-arylacetamides yielding alkenylation products of the aromatic rings in the given amino derivatives. The regio- and stereoselectivity of electrophilic aromatic substitution was investigated involving vinyl type cations and arylammonium ions or N-arylacetamides in HSO3F.

  DOI：

  10.1134/s1070428008070063
• 作为产物：
  描述：

  五甲基苯 、 4-苯基-3-丁炔-2-酮 在 hafnium(IV) trifluoromethanesulfonate 1-n-butyl-3-methylimidazolium hexafluoroantimonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以67%的产率得到(2Z)-4-(pentamethylphenyl)-4-phenyl-3-buten-2-one
  参考文献：
  名称：

  金属三氟甲磺酸催化离子液体中芳烃与炔烃的区域选择性和立体选择性Friedel-Crafts芳烃的烯化反应：范围和机理

  摘要：

  在金属三氟甲磺酸酯催化的炔烃加氢芳基化中，采用离子液体显着增强了催化活性，从而扩大了底物（芳烃和炔烃）的范围。在某些情况下，甚至在常规有机溶剂中不可能发生的反应在离子液体中也能顺利进行。而且，通过在反应后简单地倾析有机层，可以容易地回收含离子液体的催化剂，并且可以将其重新用于随后的运行中而没有任何明显的活性损失。包括反应中间体的13 C NMR分析和同位素实验在内的机理研究首次证实，这种类型的反应是通过乙烯基阳离子中间体进行的。

  DOI：

  10.1002/adsc.200700039

文献信息

• Novel Pd(II)- and Pt(II)-Catalyzed Regio- and Stereoselective <i>trans</i>-Hydroarylation of Alkynes by Simple Arenes
  作者：Chengguo Jia、Wenjun Lu、Juzo Oyamada、Tsugio Kitamura、Kenji Matsuda、Masahiro Irie、Yuzo Fujiwara

  DOI：10.1021/ja0005845

  日期：2000.8.1

  Efficient trans-hydroarylation of alkynes by simple arenes has been realized regio- and stereoselectively at room temperature in the presence of Pd(II) or Pt(II) catalysts and a mixed solvent containing trifluoroacetic acid (TFA). Various arenes undergo trans-hydroarylation selectively across terminal and internal C-C triple bonds-including those conjugated to CHO, COMe, CO2H, and CO2Et groups, affording kinetically controlled cis-arylalkenes predominantly in most cases, especially, in good yields for electron-rich arenes and activated alkynes. The formation of arene/alkyne 1/2 or 2/1 adducts as side products is dependent on the arenes' and alkynes' substituents, which can be suppressed in some cases by changing the catalyst, catalyst concentration, and reaction time. The Pt(II) system, PtCl2/2AgOAc/TFA, shows lower catalytic activity than Pd(OAc)(2)/TFA, but higher selectivity, giving higher yields of adducts at the same conversion. On the basis of several isotope experiments and control reactions, a possible mechanism involving electrophilic metalation of aromatic C-H bonds by in-situ-generated cationic Pd(II) and Pt(II) species leading to intermolecular trans-arylpalladation to alkynes has been discussed.
• Reactions of acetylene ketones in superacids
  作者：S. A. Aristov、A. V. Vasil’ev、G. K. Fukin、A. P. Rudenko

  DOI：10.1134/s1070428007050107

  日期：2007.5

  Vinyl type cations ArC+=CHCOR generated from acetylene ketones ArC CCOR in superacids HSO3F and CF3SO3H react with diverse benzene derivatives to form alkenylation products, E-/Z-isomers of diarylpropenone structures Ar(Ar')C=CHCOR. The alkenylation of aromatic compounds with acetylene ketones in superacids occurs with the primary syn-addition of a hydrogen and an aryl residue to the acetylene bond followed by transformation of the product into anti-isomer under the conditions of the reaction.