3-(4-pentylphenyl)-1-phenylprop-2-yn-1-ol | 1133890-39-7

• 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: 3-(4-pentylphenyl)-1-phenylprop-2-yn-1-ol
• CAS: 1133890-39-7
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: UNALXPPUBHEWIF-UHFFFAOYSA-N

物化性质

• 沸点：
  425.5±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-pentylphenyl)-1-phenylprop-2-yn-1-ol 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以97%的产率得到1-phenyl-3-(4-pentylphenyl)-2-propyn-1-one
  参考文献：
  名称：

  Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone O-Methyl Oximes

  摘要：

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.

  DOI：

  10.1021/jo5008702
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 3-(4-pentylphenyl)-1-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes

  摘要：

  In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.

  DOI：

  10.1021/jo900102w

文献信息

• Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes
  作者：C. Wade Downey、Brian D. Mahoney、Vincent R. Lipari

  DOI：10.1021/jo900102w

  日期：2009.4.3

  In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.
• Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone <i>O</i>-Methyl Oximes
  作者：Yunkyung Jeong、Bom-I Kim、Jae Kyun Lee、Jae-Sang Ryu

  DOI：10.1021/jo5008702

  日期：2014.7.18

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.