2-(4-methoxyphenyl)-1-(1-methyl-1H-indol-3-yl)-1,2,3,4-tetrahydroisoquinoline | 1338367-24-0

• 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: 2-(4-methoxyphenyl)-1-(1-methyl-1H-indol-3-yl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-methoxyphenyl)-1-(1-methylindol-3-yl)-3,4-dihydro-1H-isoquinoline
• CAS: 1338367-24-0
• 化学式: C₂₅H₂₄N₂O
• 分子量: 368.478
• InChiKey: TVIWQHGSKBKJPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基苯酚 在 碘苯二乙酸 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 0.5h， 生成 2-(4-methoxyphenyl)-1-(1-methyl-1H-indol-3-yl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  仲环胺的α-Csp3-H键的氧化还原中性官能化：N-芳基化/形式的交叉脱氢偶联的一种高度原子经济的策略

  摘要：

  一种有效的氧化还原中性方法已发展为α-CSP 3仲环胺的官能-H经由并发Ñ -arylation /正式横脱氢耦合（CDC）与SP 2 -C-H和SP 3 -C-H键的芳烃和酮。所开发的协议操作简单，高度原子经济且对环境无害（E因子=约0.5）。基于控制实验和通过质谱法检查反应性中间体，已经解释了反应机理。

  DOI：

  10.1039/d0gc04258g

文献信息

• Cross dehydrogenative coupling of <i>N</i>-aryltetrahydroisoquinolines (sp³ C–H) with indoles (sp² C–H) using a heterogeneous mesoporous manganese oxide catalyst
  作者：B. Dutta、V. Sharma、N. Sassu、Y. Dang、C. Weerakkody、J. Macharia、R. Miao、A. R. Howell、S. L. Suib

  DOI：10.1039/c7gc01919j

  日期：——

  heterogeneous catalytic approach for selective coupling of C1 of N-aryltetrahydroisoquinolines with C3 of indoles in the presence of mesoporous manganese oxides. Our work involves a detailed mechanistic investigation of the reaction on the catalyst surface, backed by DFT computational studies, to understand the superior catalytic activity of manganese oxides.

  我们公开了一种新颖的，非均相的催化方法，用于在介孔锰氧化物的存在下将N-芳基四氢异喹啉的C1与吲哚的C3进行选择性偶联。我们的工作包括在DFT计算研究的支持下，对催化剂表面反应的详细机理研究，以了解锰氧化物的优异催化活性。
• Cobalt(II)/<i>N</i>-Hydroxyphthalimide-Catalyzed Cross-Dehydrogenative Coupling Reaction at Room Temperature under Aerobic Condition
  作者：Mahendra R. Patil、Noopur P. Dedhia、Anant R. Kapdi、A.Vijay Kumar

  DOI：10.1021/acs.joc.8b00203

  日期：2018.4.20

  This work reports a cobalt(II)/N-hydroxyphthalimide (NHPI)-catalyzed cross-dehydrogenative oxidative coupling of N-aryl tetrahydroisoquinolines with various pro-nucleophiles, such as indoles, nitroalkanes, and trialkylphosphites, active methylene compounds, and other nucleophiles, such as cyanide (ethyl cyanoformate), at room temperature under aerobic conditions. The present protocol is operationally

  这项工作报道了钴（II​​）/ N-羟基邻苯二甲酰亚胺（NHPI）催化的N-芳基四氢异喹啉与各种亲核试剂如吲哚，硝基烷和三烷基亚磷酸酯，活性亚甲基化合物和其他亲核试剂的交叉脱氢氧化偶联，如氰化物（氰基甲酸乙酯），在室温下好氧的条件下。本方案操作简单，可以在无光辐照的情况下和在无过氧化物的条件下进行，甚至以克为单位，以提供良好至优异收率的产物。在质谱和控制实验的基础上，提出了催化反应途径。
• Acetic Acid Promoted Metal-Free Aerobic Carbon–Carbon Bond Forming Reactions at α-Position of Tertiary Amines
  作者：Hirofumi Ueda、Kei Yoshida、Hidetoshi Tokuyama

  DOI：10.1021/ol5018883

  日期：2014.8.15

  The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.
• Solvent-Free Cross-Dehydrogenative Coupling Reactions under High Speed Ball-Milling Conditions Applied to the Synthesis of Functionalized Tetrahydroisoquinolines
  作者：Weike Su、Jingbo Yu、Zhenhua Li、Zhijiang Jiang

  DOI：10.1021/jo2015533

  日期：2011.11.4

  Solvent-free reaction using a high-speed ball milling technique has been first applied to cross-dehydrogenative coupling (CDC) reactions between tetrahydroisoquinolines and three types of pronucleophiles such as nitroalkanes, alkynes, and indoles. All coupling products were obtained in good yields at short reaction times (no more than 40 min). When alkynes and indoles were used as pronucleophile, the reactions can be catalyzed efficiently by recoverable copper balls without any additional metal catalyst.
• Redox-neutral functionalization of α-Csp³–H bonds of secondary cyclic amines: a highly atom-economical strategy for <i>N</i>-arylation/formal cross-dehydrogenative couplings
  作者：Priyankar Jha、Saddam Husen、Ravindra Kumar

  DOI：10.1039/d0gc04258g

  日期：——

  An efficient redox-neutral method has been developed for α-Csp3–H functionalization of secondary cyclic amines via concurrent N-arylation/formal cross dehydrogenation coupling (CDC) with sp2-C–H and sp3-C–H bonds of arenes and ketones, respectively. The developed protocol is operationally simple, highly atom economical and environmentally benign (E-factor = ca. 0.5). The reaction mechanism has been

  一种有效的氧化还原中性方法已发展为α-CSP 3仲环胺的官能-H经由并发Ñ -arylation /正式横脱氢耦合（CDC）与SP 2 -C-H和SP 3 -C-H键的芳烃和酮。所开发的协议操作简单，高度原子经济且对环境无害（E因子=约0.5）。基于控制实验和通过质谱法检查反应性中间体，已经解释了反应机理。