1-Ethynyl-2-((E)-2-phenyl-propenyl)-benzene | 798553-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-Ethynyl-2-((E)-2-phenyl-propenyl)-benzene
• 英文别名: 1-Ethynyl-2-(2-phenylprop-1-en-1-yl)benzene；1-ethynyl-2-(2-phenylprop-1-enyl)benzene
• CAS: 798553-39-6
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: PMEJAEGKPNGITL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Ethynyl-2-((E)-2-phenyl-propenyl)-benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(o-ethynylphenyl)-2-methyl-2-phenyl-oxirane 、 1-(o-ethynylphenyl)-2-methyl-2-phenyl-oxirane
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclization of Alkyne−Epoxide Functionalities through Alternation of the Substituent and Structural Skeleton of Epoxides

  摘要：

  Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh(3)(CH3CN)(2)PF6 catalyst (10 mol %) in hot toluene (100 degreesC, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives and carbon monoxide efficiently. The cyclization of 1-cis-enynyl-2-alkyl epoxides with this catalyst in hot toluene (10 mol %, 100 degreesC, 12 h) gave 2,5-disubstituted phenols in 45-72% yields. Under the same conditions, 1-cis-enynyl-2,2-dialkyl epoxides and 1-cis-enynyl-2-alkyl-2-aryl epoxides gave the corresponding 6,6-disubstituted cyclohexa-2,4-dien-1-ones in good yields (85-91%). Mechanisms for these new cyclization reactions are proposed on the basis of trapping experiments and isotope labeling experiments. The formation of 1H-indene products likely involves ruthenium-acyl intermediates whereas cyclohexa-2,4-dien-1-ones are thought to derive from ruthenium-ketene intermediates.

  DOI：

  10.1021/jo048983w
• 作为产物：
  描述：

  (1-phenylethyl)triphenylphosphonium bromide 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 1-Ethynyl-2-((E)-2-phenyl-propenyl)-benzene
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclization of Alkyne−Epoxide Functionalities through Alternation of the Substituent and Structural Skeleton of Epoxides

  摘要：

  Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh(3)(CH3CN)(2)PF6 catalyst (10 mol %) in hot toluene (100 degreesC, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives and carbon monoxide efficiently. The cyclization of 1-cis-enynyl-2-alkyl epoxides with this catalyst in hot toluene (10 mol %, 100 degreesC, 12 h) gave 2,5-disubstituted phenols in 45-72% yields. Under the same conditions, 1-cis-enynyl-2,2-dialkyl epoxides and 1-cis-enynyl-2-alkyl-2-aryl epoxides gave the corresponding 6,6-disubstituted cyclohexa-2,4-dien-1-ones in good yields (85-91%). Mechanisms for these new cyclization reactions are proposed on the basis of trapping experiments and isotope labeling experiments. The formation of 1H-indene products likely involves ruthenium-acyl intermediates whereas cyclohexa-2,4-dien-1-ones are thought to derive from ruthenium-ketene intermediates.

  DOI：

  10.1021/jo048983w

文献信息

• Gold(I) Catalysis Applied to the Stereoselective Synthesis of Indeno[2,1-<i>b</i>]thiochromene Derivatives and Seleno Analogues
  作者：Cintia Virumbrales、Mahmoud A. E. A. A. A. El-Remaily、Samuel Suárez-Pantiga、Manuel A. Fernández-Rodríguez、Félix Rodríguez、Roberto Sanz

  DOI：10.1021/acs.orglett.2c03411

  日期：2022.11.4

  synthesis of sulfur- or selenium-containing indeno[1,2-b]chromene derivatives from o-(alkynyl)styrenes substituted at the triple bond with a thio- or seleno-aryl group is described. The reaction involves a double cyclization process through a proposed key gold–cyclopropyl carbene intermediate that evolves by the intramolecular addition of an aromatic to the cyclopropane ring, affording polycyclic structures

  金 (I) 催化的级联反应，用于立体选择性合成含硫或含硒的茚并 [1,2- b ] 色烯衍生物，从邻（炔基）苯乙烯在三键处被硫代或硒代芳基取代组进行了说明。该反应涉及通过提出的关键金-环丙基卡宾中间体的双环化过程，该中间体通过将芳族化合物分子内加成到环丙烷环上而形成，提供多环结构。使用带有手性配体的金 (I) 配合物研究了对映选择性版本。
• Ruthenium-Catalyzed Cyclization of Alkyne−Epoxide Functionalities through Alternation of the Substituent and Structural Skeleton of Epoxides
  作者：Lin Ming-Yuan、Reniguntala J. Madhushaw、Rai-Shung Liu

  DOI：10.1021/jo048983w

  日期：2004.10.1

  Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh(3)(CH3CN)(2)PF6 catalyst (10 mol %) in hot toluene (100 degreesC, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives and carbon monoxide efficiently. The cyclization of 1-cis-enynyl-2-alkyl epoxides with this catalyst in hot toluene (10 mol %, 100 degreesC, 12 h) gave 2,5-disubstituted phenols in 45-72% yields. Under the same conditions, 1-cis-enynyl-2,2-dialkyl epoxides and 1-cis-enynyl-2-alkyl-2-aryl epoxides gave the corresponding 6,6-disubstituted cyclohexa-2,4-dien-1-ones in good yields (85-91%). Mechanisms for these new cyclization reactions are proposed on the basis of trapping experiments and isotope labeling experiments. The formation of 1H-indene products likely involves ruthenium-acyl intermediates whereas cyclohexa-2,4-dien-1-ones are thought to derive from ruthenium-ketene intermediates.