1-allyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline | 1227403-17-9

• 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: 1-allyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-methoxyphenyl)-1-prop-2-enyl-3,4-dihydro-1H-isoquinoline
• CAS: 1227403-17-9
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: DHUGDMVIUXCXME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  12.5
• 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 potassium phosphate 、 copper(l) iodide 、 氧气 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 、 异丙醇 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 144.0h， 生成 1-allyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Acetic Acid Promoted Metal-Free Aerobic Carbon–Carbon Bond Forming Reactions at α-Position of Tertiary Amines

  摘要：

  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.

  DOI：

  10.1021/ol5018883

文献信息

• Direct sp³ C–H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(<scp>iii</scp>) under mild conditions
  作者：Wataru Muramatsu、Kimihiro Nakano、Chao-Jun Li

  DOI：10.1039/c3ob42354a

  日期：——

  We have developed a method for the sp3 C–H bond functionalization of tetrahydroisoquinolines (THIQs) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA). The treatment of the THIQs with various nucleophiles in the presence of PIFA in a green solvent alternative gave the coupled products, with a C–C, C–N, or quaternary carbon center in high yields.

  我们已经开发了一种由[双（三氟乙酰氧基）碘]苯（PIFA）介导的四氢异喹啉（THIQs）的sp 3 C–H键官能化的方法。在绿色溶剂替代方案中，在PIFA存在下，用各种亲核试剂处理THIQs，可得到具有高收率的C–C，C–N或季碳中心的偶联产物。
• 8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights
  作者：Antonio Casado-Sánchez、Mustafa Uygur、Daniel González-Muñoz、Fernando Aguilar-Galindo、José Luis Nova-Fernández、Judith Arranz-Plaza、Sergio Díaz-Tendero、Silvia Cabrera、Olga García Mancheño、José Alemán

  DOI：10.1021/acs.joc.9b00520

  日期：2019.5.17

  A family of quinoline–platinum(II) complexes as efficient photocatalysts is presented. Their key characteristic is their easy preparation by coordination of the readily available 8-hydroxy- or 8-thio-quinoline ligands, which are well known for their strong chelating ability to different metal ions. In the different photochemical transformations investigated, such as cross-dehydrogenative coupling,

  介绍了一种喹啉-铂（II）配合物作为有效的光催化剂。它们的关键特征是通过容易获得的8-羟基-或8-硫代喹啉配体的配位可轻松制备，这些配体因其对不同金属离子的强螯合能力而闻名。在研究的不同光化学转化中，例如交叉脱氢偶联，芳基硼酸的氧化和醛的不对称烷基化，8-巯基喹啉-Pt（II）络合物被证明是最通用的催化剂。此外，猝灭实验表明，与文献报道的相关方法相反，这些配合物在所有研究的转化中均遵循氧化猝灭机理。除了，
• Carbon Nitride-Catalyzed Photoredox Sakurai Reactions and Allylborations
  作者：Lennart Möhlmann、Siegfried Blechert

  DOI：10.1002/adsc.201400551

  日期：2014.9.15

  photocatalytic, oxidative CC coupling has grown to a well‐established methodology, especially for the modification of aryl‐substituted tetrahydroisoquinoline derivatives. However, until now, this reaction is mainly restricted to the usage of strong nucleophiles like nitroalkanes, cyanides, enamines, phosphonates and malonates. Within this publication we present an extension of such a method towards

  在过去的几年中，光催化的C CC偶联已经发展成为一种完善的方法，特别是用于芳基取代的四氢异喹啉衍生物的修饰。但是，到目前为止，该反应主要限于使用强亲核试剂，如硝基烷，氰化物，烯胺，膦酸酯和丙二酸酯。在该出版物中，我们介绍了这种方法的扩展，适用于较弱的亲核试剂，即烯丙基锡烷，烯丙基硅烷和烯丙基硼烷。因此，发明了一种非常简单的方案，使用非均质中孔石墨氮化碳（mpg-C 3 N 4）作为催化剂，空气作为氧化剂，从而为多种基材提供了高收率。
• C–H allylation of N-aryl-tetrahydroisoquinolines by merging photoredox catalysis with iodide catalysis
  作者：Zhujia Feng、Tingting Zeng、Jun Xuan、Yunhang Liu、Liangqiu Lu、Wen-Jing Xiao

  DOI：10.1007/s11426-015-5548-x

  日期：2016.2

  A dual catalytic system, combing visible light photoredox catalysis and iodide catalysis, has been developed for the functionalization of inert C–H bonds. By doing so, radical allylation reactions of N-aryl-tetrahydroisoquinolines (THIQs) were realized under extremely mild conditions, affording a wide variety of allyl-substituted THIQs in up to 78% yields.

  针对惰性 C-H 键的功能化，我们开发了一种结合了可见光光氧化催化和碘化物催化的双重催化系统。通过这种方法，在极其温和的条件下实现了 N-芳基-四氢异喹啉（THIQs）的自由基烯丙基化反应，得到了多种烯丙基取代的 THIQs，收率高达 78%。
• FeCl₃-Catalyzed Oxidative Allylation of sp² and sp³ C−H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines
  作者：Gullapalli Kumaraswamy、Akula Narayana Murthy、Arigala Pitchaiah

  DOI：10.1021/jo1005813

  日期：2010.6.4

  Oxidative allylation to sp(2)- and sp(3)-carbon attached to the nitrogen atom was accomplished. The alpha-allylation of tertiary amines was catalyzed by easily available hydrated iron(III) chloride in combination with air or aqueous (BuOOH)-Bu-t. Remarkably, N-allyl- and N-propagyl-tethered tertiary amines were also allylated through this protocol.