3,3-dimethyl-1,6-diphenyl-hex-5-yne-1,4-dione | 1072824-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dimethyl-1,6-diphenyl-hex-5-yne-1,4-dione
• 英文别名: 3,3-Dimethyl-1,6-diphenylhex-5-yne-1,4-dione
• CAS: 1072824-19-1
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: HDQOXQKJMMKQMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4-dimethyl-1,6-diphenylhexa-1,5-diyn-3-one 在 三苯基膦氯金 、 水 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以45%的产率得到4-benzoyl-5,5-dimethyl-3-phenyl-cyclopent-2-enone
  参考文献：
  名称：

  Gold-Catalyzed Hydrative Carbocyclization of 1,5- and 1,6-Diyn-3-ones via an Oxygen Transfer Process

  摘要：

  This study reports new hydrative carbocyclizations of 1,5- and 1,6-diyn-3-ones catalyzed by PPh3AuOTf, involving a pi-alkyne-assisted oxygen transfer in the reaction mechanisms. Treatment of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes with PPh3AuOTf (5 mol %) in wet 1,4-dioxane (23 degrees C, 10 min) led to hydrative aromatization to give 4-hydroxyl-1-naphthyl ketones efficiently. This approach is also extendible to the hydrative cyclization of acyclic 1,5-diyn-3-ones, which afforded 4-cyclopentenonyl ketones in reasonable yields. On the basis of this oxygen-labeling study, we propose a plausible mechanism involving an alkyne-assisted oxygen transfer to generate key oxonium and gold-enolate intermediates.

  DOI：

  10.1021/jo801753g

文献信息

• Gold-Catalyzed Hydrative Carbocyclization of 1,5- and 1,6-Diyn-3-ones via an Oxygen Transfer Process
  作者：Jhih-Meng Tang、Ting-An Liu、Rai-Shung Liu

  DOI：10.1021/jo801753g

  日期：2008.11.7

  This study reports new hydrative carbocyclizations of 1,5- and 1,6-diyn-3-ones catalyzed by PPh3AuOTf, involving a pi-alkyne-assisted oxygen transfer in the reaction mechanisms. Treatment of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes with PPh3AuOTf (5 mol %) in wet 1,4-dioxane (23 degrees C, 10 min) led to hydrative aromatization to give 4-hydroxyl-1-naphthyl ketones efficiently. This approach is also extendible to the hydrative cyclization of acyclic 1,5-diyn-3-ones, which afforded 4-cyclopentenonyl ketones in reasonable yields. On the basis of this oxygen-labeling study, we propose a plausible mechanism involving an alkyne-assisted oxygen transfer to generate key oxonium and gold-enolate intermediates.