(9ci)-1-(4-氟苯基)-2-甲基-1H-茚 | 798553-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 中文名称: (9ci)-1-(4-氟苯基)-2-甲基-1H-茚
• 英文名称: 1-(4-fluoro-phenyl)-2-methyl-1H-indene
• 英文别名: 1-(4-Fluorophenyl)-2-methyl-1H-indene
• CAS: 798553-54-5
• 化学式: C₁₆H₁₃F
• 分子量: 224.278
• InChiKey: PDUKYMKJTNJMFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(2-ethynyl-phenyl)-2-(4-fluorophenyl)-2-methyl-oxirane 在 TpRu(PPh₃)(CH₃CN)2PF₆ 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以72%的产率得到(9ci)-1-(4-氟苯基)-2-甲基-1H-茚
  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

• 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.