1-(1-methyl-1H-pyrrol-2-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline | 1228311-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-(1-methyl-1H-pyrrol-2-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(1-methylpyrrol-2-yl)-2-phenyl-3,4-dihydro-1H-isoquinoline
• CAS: 1228311-98-5
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: NYKFSHMOFANFAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 2-苯基-1,2,3,4-四氢异喹啉 在 叔丁基过氧化氢 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以73%的产率得到1-(1-methyl-1H-pyrrol-2-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Highly efficient oxidative carbon–carbon coupling with SBA-15-support iron terpyridine catalyst

  摘要：

  SBA-15-Fe(terpy)2+ 复合物高效催化了季胺与碳亲核体的氧化 C–C 交叉偶联反应，产物产率很高。支撑的吡啶琥珀酸配体可以通过过滤回收。

  DOI：

  10.1039/c001209b

文献信息

• Simple and Sustainable Iron-Catalyzed Aerobic C–H Functionalization of <i>N</i>,<i>N</i>-Dialkylanilines
  作者：Maxim O. Ratnikov、Xinfang Xu、Michael P. Doyle

  DOI：10.1021/ja402479r

  日期：2013.6.26

  chloride catalyzes the aerobic oxidation of tertiary anilines, including tetrahydroisoquinolines, to form reactive iminium ion intermediates that undergo Mannich reactions with silyloxyfurans, nitroalkanes, and other nucleophiles to give the corresponding butenolides, nitro compounds, and α-substituted tetrahydroisoquinolines, respectively, in good to excellent yields.

  氯化铁 (III) 催化叔苯胺（包括四氢异喹啉）的有氧氧化形成活性亚胺离子中间体，该中间体与甲硅烷氧基呋喃、硝基烷烃和其他亲核试剂发生曼尼希反应，分别生成相应的丁烯内酯、硝基化合物和 α-取代的四氢异喹啉，以良好的产量。
• A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with <i>N</i>-Phenyltetrahydroisoquinoline
  作者：Esther Boess、Corinna Schmitz、Martin Klussmann

  DOI：10.1021/ja211697s

  日期：2012.3.21

  A comparative mechanistic study of Cu-catalyzed oxidative coupling reactions of N-phenyltetrahydroisoquinoline with different nucleophiles was conducted. Two previously reported combinations of catalyst and oxidant were studied, CuCl2 center dot 2H(2)O/O-2 and CuBr/tert-butyl hydroperoxide (TBHP). On the basis of a synthetic study with different nucleophiles, the electrophilicity of the intermediate iminium ion was estimated and differences between the two methods were revealed. The key intermediate in the aerobic method is shown to be an iminium ion, formed through oxidation by copper(II), which can react with any nudeophile of sufficient reactivity. The role of oxygen is the reoxidation of the reduced catalyst. In the CuBr/TBHP system, an alpha-amino peroxide is proposed as a true intermediate within the catalytic cycle, formed from the amine and TBHP by a Cu-catalyzed radical reaction pathway and acting as a precursor to the iminium ion intermediate.