6,7-dimethoxy-2-phenyl-1-(phenylethynyl)-1,2,3,4-tetrahydroisoquinoline | 1350895-86-1

• 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: 6,7-dimethoxy-2-phenyl-1-(phenylethynyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6,7-dimethoxy-2-phenyl-1-(2-phenylethynyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1350895-86-1
• 化学式: C₂₅H₂₃NO₂
• 分子量: 369.463
• InChiKey: VIECAJMMTKWWDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,7-dimethoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 copper(I) trifluoromethanesulfonate benzene 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 6,7-dimethoxy-2-phenyl-1-(phenylethynyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  可见光促进四氢异喹啉在流动中的光氧化还原C（sp3）–H键功能化

  摘要：

  流动中进行的有机催化和可见光氧化还原催化的合并，允许在正式的C–H氧化/曼尼希反应中使用各种官能化的N-芳基取代的四氢异喹啉（THIQs）。几种N-芳基取代的THIQ的Strecker型官能化和铜催化的炔基化也已成功进行，从而获得了有价值的高效率产品。事实证明，使用定制的多孔聚合物型微反应器对于C–H氧化步骤和整体反应性能至关重要。

  DOI：

  10.1039/d0ob02582h

文献信息

• Three-component, four-centered, one-pot synthesis of 1-(arylethynyl)-2,3,4,9-tetrahydro-1 H -pyrido[3,4- b ]indole derivatives
  作者：B.V. Subba Reddy、Kavya Kota、R. Anji Babu、P. Rasvan Khan、K. Mukkanti

  DOI：10.1016/j.tetlet.2017.04.008

  日期：2017.5

  three component, four-centered A3 coupling strategy has been developed for the synthesis of a novel series of 1-arylethynyl-tetrahydro-β-carboline derivatives in good yields with high selectivity. This method is also useful for the preparation of 1-arylethynyl tetrahydroisoquinolines, which can be used for the synthesis of biologically active molecules such as homolaudanosine, dysoxyline, methopoline

  已经开发了一种有效的三组分，四中心的A3偶联策略，用于以高收率和高选择性合成一系列新的1-芳基乙炔基-四氢-β-咔啉衍生物。该方法也可用于制备1-芳基乙炔基四氢异喹啉，其可用于合成生物活性分子，例如高月桂木苷，dysoxyline，甲氧茶碱和almorexant。使用现成的ZnCl 2 / Et 3 N试剂系统使该方法简单，方便和实用。
• 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。
• Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light
  作者：David B. Freeman、Laura Furst、Allison G. Condie、Corey R. J. Stephenson

  DOI：10.1021/ol202883v

  日期：2012.1.6

  Our previous studies into visible-light-mediated aza-Henry reactions demonstrated that molecular oxygen played a vital role in catalyst turnover as well as the production of base to facilitate the nucleophilic addition of nitroalkanes. Herein, improved conditions for the generation of iminium Ions from tetrahydroisoquinolines that allow for versatile nucleophilic trapping are reported. The new conditions provide access to a diverse range of functionality under mild, anaerobic reaction conditions as well as mechanistic insights into the photoredox cycle.
• 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.
• Visible light promoted photoredox C(sp³)–H bond functionalization of tetrahydroisoquinolines in flow
  作者：Ana Filipović、Zdravko Džambaski、Dana Vasiljević-Radović、Bojan P. Bondžić

  DOI：10.1039/d0ob02582h

  日期：——

  A merger of organocatalysis and visible light photoredox catalysis performed in flow allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) in a formal C–H oxidation/Mannich reaction. Strecker type functionalization and copper-catalyzed alkynylation of several N-aryl-substituted THIQs were also successfully performed in flow, giving valuable products with

  流动中进行的有机催化和可见光氧化还原催化的合并，允许在正式的C–H氧化/曼尼希反应中使用各种官能化的N-芳基取代的四氢异喹啉（THIQs）。几种N-芳基取代的THIQ的Strecker型官能化和铜催化的炔基化也已成功进行，从而获得了有价值的高效率产品。事实证明，使用定制的多孔聚合物型微反应器对于C–H氧化步骤和整体反应性能至关重要。