2-phenyl-1-(p-tolylethynyl)-1,2,3,4-tetrahydroisoquinoline | 1418605-32-9

• 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-phenyl-1-(p-tolylethynyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-[2-(4-methylphenyl)ethynyl]-2-phenyl-3,4-dihydro-1H-isoquinoline
• CAS: 1418605-32-9
• 化学式: C₂₄H₂₁N
• 分子量: 323.437
• InChiKey: DEMLNEBJNKLJKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  碘苯 在 potassium dihydrogenphosphate 、 copper(l) iodide 、 4-二甲氨基苯甲酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 36.0h， 生成 2-phenyl-1-(p-tolylethynyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Metal-free polyporphyrin based photocatalysts for the functionalization of C(sp³)–H bonds in water

  摘要：

  使用不溶性的多吡咯或水分散的纳米多吡咯，可以在温和条件下在水中实现C(sp³)–H键的可见光诱导的官能化。

  DOI：

  10.1039/d2cc04352a

文献信息

• Electrocatalytic C(sp³)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis
  作者：Bin Guo、Hai-Chao Xu

  DOI：10.3762/bjoc.17.178

  日期：——

  Electrocatalytic dehydrogenative C(sp³)–H/C(sp)–H cross-coupling of tetrahydroisoquinolines with terminal alkynes has been achieved in a continuous-flow microreactor through 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)/copper relay catalysis. The reaction is easily scalable and requires low concentration of supporting electrolyte and no external chemical oxidants or ligands, providing straightforward and sustainable access to 2-functionalized tetrahydroisoquinolines.

  已实现通过2,2,6,6-四甲基哌啶1-氧自由基（TEMPO）/铜中继催化，在连续流微反应器中进行四氢异喹啉与末端炔烃的电催化脱氢C(sp3)–H/C(sp)–H交叉偶联。该反应易于扩展规模，需要低浓度的支持电解质，无需外部化学氧化剂或配体，可直接且可持续地获得2-官能化的四氢异喹啉。
• Dual Catalysis: Combination of Photocatalytic Aerobic Oxidation and Metal Catalyzed Alkynylation Reactions-CC Bond Formation Using Visible Light
  作者：Magnus Rueping、René M. Koenigs、Konstantin Poscharny、David C. Fabry、Daniele Leonori、Carlos Vila

  DOI：10.1002/chem.201200050

  日期：2012.4.23

  Shedding new light on the right combination of catalysts: A new dual catalytic system for efficient CH functionalization was developed. The appropriate choice of two metal catalysts allows the oxidative alkynylation of tertiary amines under mild and sustainable reaction conditions.

  为正确的催化剂组合提供了新的亮点：开发了一种新型的双催化体系，可实现高效的CH功能化。两个金属催化剂的适当选择允许温和和可持续的反应条件下叔胺的氧化炔基。
• Selective trifluoromethylation and alkynylation of tetrahydroisoquinolines using visible light irradiation by Rose Bengal
  作者：Weijun Fu、Wenbo Guo、Guanglong Zou、Chen Xu

  DOI：10.1016/j.jfluchem.2012.05.009

  日期：2012.8

  convenient and efficient method for oxidative coupling of tetrahydroisoquinoline derivatives with trimethyl(trifluoromethyl)silane and terminal alkynes to 1-trifluoromethylated or 1-alkynylated tetrahydroisoquinolines via CH activation was developed using visible light irradiation. The protocol uses Rose Bengal as the catalyst, air as terminal oxidant, and the trifluoromethylation or alkynylation was selectively

  利用可见光照射，开发了一种方便有效的方法，将四氢异喹啉衍生物与三甲基（三氟甲基）硅烷和末端炔烃经C H活化氧化偶联为1-三氟甲基化或1-炔基化四氢异喹啉。该方案使用玫瑰红作为催化剂，空气作为末端氧化剂，三氟甲基化或炔基化反应是在极温和的条件下在氮的α位选择性进行的。
• Photoredox catalytic organic reactions promoted with broadband visible light-absorbing Bodipy-iodo-aza-Bodipy triad photocatalyst
  作者：Song Guo、Renjie Tao、Jianzhang Zhao

  DOI：10.1039/c4ra03631j

  日期：——

  Bodipy-diiodo aza-Bodipy triad showing broadband visible light-absorption was used as efficient photocatalyst for photoredox catalytic organic reactions.

  Bodipy-diiodo aza-Bodipy三联物显示宽带可见光吸收，被用作高效光催化剂，用于光氧化还原催化有机反应。
• 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.