1-((4-fluorophenyl)ethynyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline | 1418605-33-0

• 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: 1-((4-fluorophenyl)ethynyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(2-(4-fluorophenyl)ethynyl)-1,2,3,4-tetrahydro-2-phenylisoquinoline；1-[2-(4-fluorophenyl)ethynyl]-2-phenyl-3,4-dihydro-1H-isoquinoline
• CAS: 1418605-33-0
• 化学式: C₂₃H₁₈FN
• 分子量: 327.401
• InChiKey: UCSNYPSSDRYJDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氟苯乙炔 、 2-苯基-1,2,3,4-四氢异喹啉 在 2.71 wt% copper-doped carbon nitride 、 air 作用下， 以 乙腈 为溶剂， 以77 %的产率得到1-((4-fluorophenyl)ethynyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  铜掺杂氮化碳作为一种实用的多相金属光催化剂用于叔胺与末端炔烃的有氧氧化交叉偶联

  摘要：

  具有可回收催化剂的多相金属光催化化学转化对于可持续有机合成是非常理想和具有挑战性的。在此，我们构建了一种 Cu 掺杂的氮化碳 (CN-Cu) 材料，可用作 Cu-光双催化系统。非均相 CN-Cu 催化剂可用于以空气为氧化剂对叔胺进行直接 α-炔基化反应，从而以良好至优异的收率构建多种有价值的炔丙胺。Cu与CN-Cu中的光催化中心之间的内生接近和协同作用显着增强了Cu-光双催化活性，从而进一步提高了反应效率和选择性。值得注意的是，这种多相催化剂表现出很高的化学稳定性，并且可以循环使用至少五次而不会损失活性。

  DOI：

  10.1039/d3gc01247f

文献信息

• 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.
• Fast, solvent-free asymmetric alkynylation of prochiral sp3 C–H bonds in a ball mill for the preparation of optically active tetrahydroisoquinoline derivatives
  作者：Jingbo Yu、Zhenhua Li、Kanyan Jia、Zhijiang Jiang、Menglu Liu、Weike Su

  DOI：10.1016/j.tetlet.2013.02.007

  日期：2013.4

  Solvent-free asymmetric cross-dehydrogenative-coupling (CDC) reaction between the sp(3) C-H bond of prochiral CH2 and terminal alkynes was first studied under High-Speed Ball-Milling conditions. A series of optical active 1-alkynyl tetrahydroisoquinoline derivatives were achieved by using recoverable copper balls together with PyBox chiral ligand in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). All coupling products were obtained in good yields at short reaction time with enantiomeric excesses up to 79%. (C) 2013 Elsevier Ltd. All rights reserved.