1-(2-(hex-1-ynyl)phenyl)-3-phenylprop-2-yn-1-one | 1072823-72-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-(hex-1-ynyl)phenyl)-3-phenylprop-2-yn-1-one
• 英文别名: 1-(2-Hex-1-ynylphenyl)-3-phenylprop-2-yn-1-one
• CAS: 1072823-72-3
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: VXKYPDOTASEUGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  1-(2-(hex-1-ynyl)phenyl)-3-phenylprop-2-yn-1-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 24.0h， 以38%的产率得到1-(4-hydroxy-2-phenylnaphthalen-1-yl)pentan-1-one
  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

• Synthesis of Polysubstituted Naphthofurans and Indenofurans Based on a Regiodivergent Intramolecular Carbometalation Strategy with 2‐(2’‐Alkynylaryl)‐3‐iodofurans
  作者：Azusa Kondoh、Kohei Aita、Masahiro Terada

  DOI：10.1002/chem.202300132

  日期：——

  Efficient methods for the synthesis of two types of furan-fused tricyclic compounds were developed based on a regiodivergent intramolecular carbometalation strategy using 2-(2’-alkynylaryl)-3-iodofurans as a common substrate. The methods involving the 6-endo-anti carbocupration or the formal intramolecular 5-exo-anti carbopalladation provide new access to a wide range of well-organized polysubstituted

  基于使用 2-(2'-炔基芳基)-3-碘呋喃作为常见底物的区域发散分子内碳金属化策略，开发了两种类型的呋喃稠合三环化合物的有效合成方法。涉及 6-endo- anti carbocupration 或正式分子内 5-exo- anti carbopalladation的方法为广泛的组织良好的多取代萘并[1,2- b ]呋喃和茚并[1,2- b ]提供了新途径否则难以获得的呋喃。
• 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.