9-((2-bromophenyl)methyl)-9H-fluorene | 187754-47-8

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-((2-bromophenyl)methyl)-9H-fluorene
• 英文别名: 9-(2-bromobenzyl)-9H-fluorene；9-[(2-bromophenyl)methyl]-9H-fluorene
• CAS: 187754-47-8
• 化学式: C₂₀H₁₅Br
• 分子量: 335.243
• InChiKey: NMRVZUOQBGOFDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-((2-bromophenyl)methyl)-9H-fluorene 在 palladium diacetate potassium carbonate 、 1,2-双(二苯基膦)乙烷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 25.0h， 生成 7b,8-dihydro benzo[b]fluoranthene
  参考文献：
  名称：

  二齿膦作为配体在钯催化的分子内芳基化中：分子间碱辅助质子抽象机制

  摘要：

  芳基溴化物的钯催化芳基化反应可以在温和条件下，在二齿膦（例如dppm，dppe，dppf和Xantphos）存在下进行。实验结果和DFT计算完全支持该反应，这是通过分子间质子提取进行的机理。

  DOI：

  10.1016/j.tet.2008.01.056
• 作为产物：
  描述：

  芴 、 2-溴溴苄 在 正丁基锂 作用下， 生成 9-((2-bromophenyl)methyl)-9H-fluorene
  参考文献：
  名称：

  Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation

  摘要：

  The palladium-catalyzed intramolecular arylation reaction has been applied to the synthesis of the spiro polycyclic aromatic hydrocarbons and planar polycyclic aromatic hydrocarbons by formation of a six-membered ring. The reaction proceeds more readily with aryl bromides substituted with electron-withdrawing groups by using palladium acetate in N,N-dimethylformamide as the solvent. For the less reactive-p-methoxyaryl derivatives the use of LiI as an additive was shown to give the best results. The results obtained in the cyclization of nitro derivatives 21 and 23 suggest that the second step of the cyclization reaction is not an electrophilic substitution reaction.

  DOI：

  10.1021/jo962059n

文献信息

• Unravelling a bench-stable zinc-amide compound as highly active multitasking catalyst for radical-mediated selective alk(en)ylation of unactivated carbocycles under mild conditions
  作者：Sangita Sahoo、Subarna Manna、Arnab Rit

  DOI：10.1039/d3sc06334h

  日期：——

  compound bearing an amidated imidazolium salt towards C–C bond-forming reactions utilizing an array of alcohols, ranging from aliphatic to aromatic and, attractively, even secondary alcohols. Moreover, this readily scalable protocol, which proceeds via an underdeveloped radical-mediated borrowing hydrogen protocol (an aldehyde is generated from an alcohol, and subsequent condensation with indene/fluorene

  通过C-C 键形成对未活化的有机部分进行直接官能化长期以来一直令合成化学家着迷。尽管贱金属系统在该领域稳步兴起，但在单一催化剂中实现多任务活性以在温和条件下执行多个此类功能化是具有挑战性的。为了解决这个问题，我们在此报告了一种有效的方案，首次使用天然丰富且环保的锌衍生化合物，用醇作为绿色烷化剂对茚/芴进行选择性C-烷（烯）基化。值得注意的是，这项研究揭示了带有酰胺化咪唑鎓盐的稳定锌化合物在使用一系列醇（从脂肪族到芳香族，甚至仲醇）进行C-C键形成反应方面的独特潜力。此外，这种易于扩展的方案通过基于一系列对照实验建立的不发达的自由基介导的借氢方案（由醇产生醛，随后与茚/芴缩合提供相应的烯基化产物）进行，有效在温和条件下使用低催化剂负载即可轻松实现。值得注意的是，这种方法对烷基化或烯基化产物具有显着的选择性，具有高水平的官能团耐受性和化学选择性。至关重要的是，这些锌化合物的催化活性可归因于它们
• JP2022159082A
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation
  作者：Juan J. González、Nuria García、Berta Gómez-Lor、Antonio M. Echavarren

  DOI：10.1021/jo962059n

  日期：1997.3.1

  The palladium-catalyzed intramolecular arylation reaction has been applied to the synthesis of the spiro polycyclic aromatic hydrocarbons and planar polycyclic aromatic hydrocarbons by formation of a six-membered ring. The reaction proceeds more readily with aryl bromides substituted with electron-withdrawing groups by using palladium acetate in N,N-dimethylformamide as the solvent. For the less reactive-p-methoxyaryl derivatives the use of LiI as an additive was shown to give the best results. The results obtained in the cyclization of nitro derivatives 21 and 23 suggest that the second step of the cyclization reaction is not an electrophilic substitution reaction.
• Bidentate phosphines as ligands in the palladium-catalyzed intramolecular arylation: the intermolecular base-assisted proton abstraction mechanism
  作者：Sergio Pascual、Paula de Mendoza、Ataualpa A.C. Braga、Feliu Maseras、Antonio M. Echavarren

  DOI：10.1016/j.tet.2008.01.056

  日期：2008.6

  The palladium-catalyzed arylation of aryl bromides can be carried out in the presence of bidentate phosphines, such as dppm, dppe, dppf, and Xantphos under mild conditions. The experimental results and the DFT calculations fully support for this reaction a mechanism proceeding by an intermolecular proton abstraction.

  芳基溴化物的钯催化芳基化反应可以在温和条件下，在二齿膦（例如dppm，dppe，dppf和Xantphos）存在下进行。实验结果和DFT计算完全支持该反应，这是通过分子间质子提取进行的机理。