(E)-2-methyl-4-(3-phenylisoquinolin-4-yl)-3-buten-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-2-methyl-4-(3-phenylisoquinolin-4-yl)-3-buten-2-ol
• 英文别名: (E)-2-methyl-4-(3-phenylisoquinolin-4-yl)but-3-en-2-ol
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: OOVOMJISMJEAOX-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-3-丁烯-2-醇 、 (E)-tert-butyl({[2-(2-phenylethynyl)phenyl]methylidene})amine 在 palladium(II) bromide 氧气 、 碳酸氢钠 、 copper dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以34%的产率得到(E)-2-methyl-4-(3-phenylisoquinolin-4-yl)-3-buten-2-ol
  参考文献：
  名称：

  Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-Catalyzed Cyclization/Olefination

  摘要：

  A variety of 4-(l-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.

  DOI：

  10.1021/jo0261303

文献信息

• Synthesis of isoquinolines by palladium-catalyzed cyclization, followed by a Heck reaction
  作者：Qinhua Huang、Richard C. Larock

  DOI：10.1016/s0040-4039(02)00579-8

  日期：2002.5

  A variety of 4-(1-alkenyl)-3-arylisoquinolines have been prepared by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)benzaldimines, followed by alkenylation (Heck reaction) in good to excellent yields. The introduction of an ortho-methoxy group on the benzaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate improving the yields of the desired isoquinoline products. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-Catalyzed Cyclization/Olefination
  作者：Qinhua Huang、Richard C. Larock

  DOI：10.1021/jo0261303

  日期：2003.2.1

  A variety of 4-(l-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.