1-(2-methylallyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline | 1308790-33-1

• 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: 1-(2-methylallyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-methylphenyl)-1-(2-methylprop-2-enyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1308790-33-1
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: LMNOITRJFRTRES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline 、 异丁烯基三甲基硅烷 在 copper(II) chloride dihydrate 、 氧气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以78%的产率得到1-(2-methylallyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent

  摘要：

  The mechanism of an aerobic copper-catalyzed oxidative coupling reaction with N-phenyl tetrahydroisoquinoline was investigated. The oxidized species formed from the reaction of the amine with the copper catalyst were analyzed by NMR-spectroscopy. An iminium dichlorocuprate was found to be the reactive intermediate and could be structurally characterized by X-ray crystallography. The effect of methanol to effectively stabilize the iminium ion was investigated and shown to be beneficial in an oxidative allylation reaction.

  DOI：

  10.1021/ja201610c

文献信息

• Photocatalyst- and transition-metal-free α-allylation of <i>N</i>-aryl tetrahydroisoquinolines mediated by visible light
  作者：Zhuohua Li、Pengju Ma、Yongzhu Tan、Yufei Liu、Min Gao、Yujun Zhang、Bo Yang、Xuan Huang、Yuan Gao、Junmin Zhang

  DOI：10.1039/c9gc04191e

  日期：——

  electron-donor–acceptor (EDA) complex between the N-aryl tetrahydroisoquinolines and an allyl or a benzyl bromide. Irradiation with purple light triggered single-electron transfer (SET) from the N-aryl tetrahydroisoquinolines to the allyl or benzyl bromide of the EDA complex, inducing the formation of the corresponding allyl or benzyl radical and the subsequent radical–radical coupling. This approach represents

  已经实现了N-芳基四氢异喹啉的方便和有效的α-烯丙基化。仅在可见光照射下无需过渡金属或光催化剂即可实现这种转变。该机制涉及N-芳基四氢异喹啉与烯丙基或苄基溴之间的新型原位生成的电子供体-受体（EDA）络合物。紫色光的照射触发了N的单电子转移（SET）-芳基四氢异喹啉与EDA络合物的烯丙基或苄基溴，诱导相应的烯丙基或苄基自由基的形成，以及随后的自由基-自由基偶联。该方法代表了N-芳基四氢异喹啉的无光催化剂和无过渡金属的α-烯丙基和苄基官能化的第一个例子。
• 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。
• Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with <i>N</i>-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent
  作者：Esther Boess、Devarajulu Sureshkumar、Abhishek Sud、Cornelia Wirtz、Christophe Farès、Martin Klussmann

  DOI：10.1021/ja201610c

  日期：2011.6.1

  The mechanism of an aerobic copper-catalyzed oxidative coupling reaction with N-phenyl tetrahydroisoquinoline was investigated. The oxidized species formed from the reaction of the amine with the copper catalyst were analyzed by NMR-spectroscopy. An iminium dichlorocuprate was found to be the reactive intermediate and could be structurally characterized by X-ray crystallography. The effect of methanol to effectively stabilize the iminium ion was investigated and shown to be beneficial in an oxidative allylation reaction.