1-phenethyl-5,6,7,8-tetrahydroisoquinoline

• 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: 1-phenethyl-5,6,7,8-tetrahydroisoquinoline
• 英文别名: 1-(2-Phenylethyl)-5,6,7,8-tetrahydroisoquinoline
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: XBVPFLYKSROKIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2-乙烯基环己基)乙酮 在 四(三苯基膦)钯 、 正丁基锂 、 盐酸羟胺 、 sodium methylate 、 sodium acetate 、 sodium hydride 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 94.55h， 生成 1-phenethyl-5,6,7,8-tetrahydroisoquinoline
  参考文献：
  名称：

  Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes

  摘要：

  Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 degrees C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a beta-aryl moiety possibly due to the stabilizing pi-pi stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.

  DOI：

  10.3987/com-11-12396

文献信息

• Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes
  作者：Jia-Liang Zhu、Sheng-Wei Tsao

  DOI：10.3987/com-11-12396

  日期：——

  Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 degrees C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a beta-aryl moiety possibly due to the stabilizing pi-pi stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.