N-(p-nitrobenzyl)isoquinolinium bromide | 16726-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(p-nitrobenzyl)isoquinolinium bromide
• 英文别名: 2-(p-Nitrobenzyl)isoquinolinium bromide；2-(4-nitrobenzyl)isoquinolinium bromide；2-(4-nitrobenzyl)isoquinolin-2-ium bromide；2-(4-Nitro-benzyl)-isochinolinium; Bromid；2-[(4-Nitrophenyl)methyl]isoquinolin-2-ium bromide；2-[(4-nitrophenyl)methyl]isoquinolin-2-ium;bromide
• CAS: 16726-82-2
• 化学式: Br*C₁₆H₁₃N₂O₂
• 分子量: 345.195
• InChiKey: DSKJGDOYEGMMNN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-nitrobenzyl)isoquinolinium bromide 在 sodium hydroxide 、 苯甲酰溴 、 苯甲酸 作用下， 生成 2-(4,4'-dinitro-ξ-stilben-α-yl)-isoquinolinium; bromide
  参考文献：
  名称：

  Kroehnke, Chemische Berichte, 1951, vol. 84, p. 956,958

  摘要：

  DOI：
• 作为产物：
  描述：

  异喹啉 、 对硝基溴化苄 反应 6.0h， 生成 N-(p-nitrobenzyl)isoquinolinium bromide
  参考文献：
  名称：

  A One-Pot Domino Reaction for the Synthesis of 3-Arylindolizines from Pyridines, Benzyl Halides, and Dihalide-Substituted Electron-Deficient Alkenes

  摘要：

  通过一锅多米诺反应，从苄基卤化物与吡啶（或异喹啉）以及含环状或非环状二卤代取代的缺电子烯烃在碳酸钾存在下，利用原位生成的N-叶立德中间体，制备了3-芳基吲哚啉类化合物。苄基卤化物的芳环上可耐受供电子基团和吸电子基团。产率从中等到高不等。

  DOI：

  10.1055/s-0030-1258266

文献信息

• A New Focused Microwave Approach to the Synthesis of Amino-Substituted Pyrroloisoquinolines and Pyrroloquinolines via a Sequential Multi-Component Coupling Process
  作者：Steven Ley、Mark Hopkin、Ian Baxendale

  DOI：10.1055/s-2008-1067048

  日期：2008.6

  A multi-component reaction has been developed allowing direct access to pyrroloisoquinolines and pyrroloquinolines with new, electron-rich substitution patterns. The synthesised amino-substituted heterocyclic compounds and intermediates involved in their formation represent novel compounds. Focused microwave irradiation was used extensively to allow simple access to a wide temperature range using low boiling point solvents.

  已开发出一种多组分反应，可直接合成具有新型、富电子取代模式的吡咯并异喹啉和吡咯并喹啉。合成的氨基取代杂环化合物及其形成过程中的中间体均为新型化合物。通过使用低沸点溶剂，大量采用聚焦微波辐射，简单实现了广泛的温度范围。
• Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles
  作者：Meimei Zhou、Keyang Yu、Jianxin Liu、Weimei Shi、Yingming Pan、Haitao Tang、Xiangjun Peng、Qian Liu、Hengshan Wang

  DOI：10.1039/d1ra01226f

  日期：——

  Selective C1–H/C4–H carbonylation of N-methylene iminium salts, catalyzed by visible-light photoredox and oxygen in the air, has been reported. A ruthenium complex acts as a chemical switch to conduct two different reaction pathways and to afford two different kinds of products. In the absence of the ruthenium complex, the Csp2–H bonds adjacent to the nitrogen atoms are oxidized to α-lactams by the

  已经报道了由可见光光氧化还原和空气中的氧气催化的N-亚甲基亚胺盐的选择性 C1-H/C4-H 羰基化。钌络合物充当化学开关以进行两种不同的反应途径并提供两种不同的产物。在没有钌络合物的情况下，与氮原子相邻的 Csp 2 -H 键被N-亚甲基亚胺底物本身作为光敏剂氧化成 α-内酰胺。在钌络合物的存在下，喹啉鎓的氧化反应位点切换到C4区域，导致4-喹诺酮类的形成。在空气气氛下，使用两种转化将氧直接引入氮杂环骨架中。
• Construction of C(sp²)–X (X = Br, Cl) Bonds through a Copper-Catalyzed Atom-Transfer Radical Process: Application for the 1,4-Difunctionalization of Isoquinolinium Salts
  作者：Qiu Sun、Yuan-Yuan Zhang、Jing Sun、Ying Han、Xiaodong Jia、Chao-Guo Yan

  DOI：10.1021/acs.orglett.7b03751

  日期：2018.2.16

  A highly efficient Cu-catalyzed 1,4-difunctionalization of isoquinolinium salts was developed with ether and X– (X = Br, Cl) as the halogen source under mild conditions. This transformation involves the combination of oxidative coupling and copper-catalyzed halogen atom-transfer radical processes. This method not only provides an efficient way to prepare various substituted azaarenes but also achieves

  在温和条件下，以醚和X –（X = Br，Cl）作为卤素源，开发了一种高效的Cu催化的异喹啉鎓盐的1,4-双官能团。该转变涉及氧化偶联和铜催化的卤素原子转移自由基过程的组合。该方法不仅提供了一种制备各种取代的氮杂芳烃的有效方法，而且还通过自由基过程实现了从卤素阴离子和亲核碳原子选择性构建C（sp 2）–X（X = Br，Cl）键。
• Electrochemical regioselective selenylation/oxidation of <i>N</i>-alkylisoquinolinium salts <i>via</i> double C(sp²)–H bond functionalization
  作者：Xiang Liu、Yajun Wang、Dan Song、Yuhan Wang、Hua Cao

  DOI：10.1039/d0cc06778d

  日期：——

  An efficient, novel, and environmentally friendly electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp2)–H bond functionalization under undivided electrolytic conditions has been developed. A series of selenide isoquinolones were easily accessed through this sustainable and clean electrochemical system. The present protocol was further extended to afford

  已开发了在不分开的电解条件下通过双C（sp 2）-H键官能化对N-烷基异喹啉鎓盐进行高效，新颖且环境友好的电化学区域选择性硒化/氧化的方法。通过这种可持续，清洁的电化学系统，很容易获得一系列硒化异喹诺酮。本方案进一步扩展为提供硒化物喹诺酮和1，3-二甲基-1 H-苯并[ d ]咪唑-2（3 H）-1。此外，抗病毒生物测定法表明化合物3j对烟草花叶病毒（TMV）表现出优异的抗病毒活性，其抑制率高达90％。
• A One-Pot Domino Reaction for the Synthesis of 3-Arylindolizines from Pyridines, Benzyl Halides, and Dihalide-Substituted Electron-Deficient Alkenes
  作者：Huayou Hu、Kunbo Shi、Rongrong Hou、Zaichao Zhang、Yulan Zhu、Jianfeng Zhou

  DOI：10.1055/s-0030-1258266

  日期：2010.12

  3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high.

  通过一锅多米诺反应，从苄基卤化物与吡啶（或异喹啉）以及含环状或非环状二卤代取代的缺电子烯烃在碳酸钾存在下，利用原位生成的N-叶立德中间体，制备了3-芳基吲哚啉类化合物。苄基卤化物的芳环上可耐受供电子基团和吸电子基团。产率从中等到高不等。