(3E)-4-(2,4,5,6-tetramethylphenyl)-3-buten-2-one | 267901-66-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (3E)-4-(2,4,5,6-tetramethylphenyl)-3-buten-2-one
• 英文别名: 4-<2'.3'.4'.6'-Tetramethyl-phenyl>-but-3-en-2-on；4-(2,3,4,6-Tetramethylphenyl)-3-buten-2-one；(E)-4-(2,3,4,6-tetramethylphenyl)but-3-en-2-one
• CAS: 267901-66-6
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: PXZVHZRZXKANST-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (3E)-4-(2,4,5,6-tetramethylphenyl)-3-buten-2-one 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 4-<2',3',4',6'-Tetramethyl-phenyl>-butan-2-ol
  参考文献：
  名称：

  Syntheses of γ-Ionone Analogues. III. Diels-Alder Reaction Involving a Mixture of 3, 4-Dimethyl-1, 3-pentadiene and 2, 3-Dimethyl-1, 3-pentadiene, and Some Derivatives from 2-Benzyloxymethyl-4, 5, 6-trimethylcyclohexa-1, 4-dienylmethanal

  摘要：

  DOI：

  10.1246/bcsj.35.45
• 作为产物：
  描述：

  2,3-二甲基-1,3-戊二烯 在 barium dihydroxide 、 sulfur 作用下， 以 水 、 苯 为溶剂， 生成 (3E)-4-(2,4,5,6-tetramethylphenyl)-3-buten-2-one
  参考文献：
  名称：

  Syntheses of γ-Ionone Analogues. III. Diels-Alder Reaction Involving a Mixture of 3, 4-Dimethyl-1, 3-pentadiene and 2, 3-Dimethyl-1, 3-pentadiene, and Some Derivatives from 2-Benzyloxymethyl-4, 5, 6-trimethylcyclohexa-1, 4-dienylmethanal

  摘要：

  DOI：

  10.1246/bcsj.35.45

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.
• Syntheses of γ-Ionone Analogues. III. Diels-Alder Reaction Involving a Mixture of 3, 4-Dimethyl-1, 3-pentadiene and 2, 3-Dimethyl-1, 3-pentadiene, and Some Derivatives from 2-Benzyloxymethyl-4, 5, 6-trimethylcyclohexa-1, 4-dienylmethanal
  作者：Atsuaki Arai、Iwao Ichikizaki

  DOI：10.1246/bcsj.35.45

  日期：1962.1

表征谱图