2-phenyl-1-(pyridin-2-ylethynyl)-1,2,3,4-tetrahydroisoquinoline | 1338367-17-1

• 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-(pyridin-2-ylethynyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(pyridin-2-ylethynyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline；2-phenyl-1-(2-pyridin-2-ylethynyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1338367-17-1
• 化学式: C₂₂H₁₈N₂
• 分子量: 310.398
• InChiKey: CGAINVIQICKTGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢异喹啉 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2,2,6,6-四甲基哌啶氧化物 、 copper(II) bis(trifluoromethanesulfonate) 、 tert-butylammonium hexafluorophosphate(V) 、 sodium t-butanolate 、 2-(二环己基膦基)联苯 作用下， 以 2,2,2-三氟乙醇 、 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 2-phenyl-1-(pyridin-2-ylethynyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Electrocatalytic C(sp³)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis

  摘要：

  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。

  DOI：

  10.3762/bjoc.17.178

文献信息

• 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.
• 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。