1,2-di-p-tolylnaphthalene | 1341128-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-di-p-tolylnaphthalene
• 英文别名: 1,2-bis(4-methylphenyl)naphthalene；1,2-Bis(4-methylphenyl)naphthalene
• CAS: 1341128-23-1
• 化学式: C₂₄H₂₀
• 分子量: 308.423
• InChiKey: AALPKGWLXGIQDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-溴-1-萘酚 在 吡啶 、 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 1,2-di-p-tolylnaphthalene
  参考文献：
  名称：

  Synthesis of 1,2-Diarylnaphthalenes by Chemoselective Suzuki-Miyaura Reactions of 2-Bromo-1-(trifluoromethanesulfonyloxy)naphthalene

  摘要：

  通过Suzuki-Miyaura反应，以1-四氢萘酮为原料经过两步制备的2-溴-1-(三氟甲烷磺酰氧)萘，可得到多种1,2-二芳基萘。反应具有极佳的化学选择性，优先发生溴位取代，而三氟甲烷磺酰氧基保持未反应状态。

  DOI：

  10.1055/s-0030-1260955

文献信息

• Regioselective synthesis of substituted naphthalenes and phenanthrenes by FeCl3-promoted annulation of aryl and naphthyl acetaldehydes with alkynes
  作者：Xiuli Bu、Longcheng Hong、Ruiting Liu、Jianquan Hong、Zhengxing Zhang、Xigeng Zhou

  DOI：10.1016/j.tet.2012.07.007

  日期：2012.9

  acetaldehydes with alkynes has been established, which provides a new and versatile straightforward procedure for the regioselective synthesis of mono-, di-, and polysubstituted naphthalenes under mild conditions. Interestingly, the present catalytic system not only differentiates between internal and terminal alkynes but also shows unprecedented complete Me3SiOH elimination selectivity for silyl alkyne substrates

  已经建立了FeCl 3促进的芳基乙醛与炔烃的环化反应，这为温和条件下单，双和多取代的萘​​的区域选择性合成提供了一种新的通用直接方法。有趣的是，本催化体系不仅在内部炔烃和末端炔烃之间进行区分，而且对甲硅烷基炔烃底物显示出前所未有的完全的Me 3 SiOH消除选择性。此外，还首次以高收率和极好的区域选择性实现了通过萘乙乙醛与内部炔烃的反应合成一系列取代的菲。
• Pd/Cu Co‐Catalyzed <i>ortho</i>‐Arylation of Aryl Iodides <i>via</i> Radical Intermediates with Aryl Diazonium Salts
  作者：Ying Fu、Liang‐Liang Guo、Xi Chen、Hao Chen、Jia‐Jia Liu、Fang‐Rong Li、Cai‐Qin Xiao、Zhengyin Du

  DOI：10.1002/adsc.202300883

  日期：2023.12.5

  A Cu/Pd co-catalyzed Catellani-type ortho arylation reaction of iodoarenes with aryl diazonium salts has been developed. Aryl radicals that derived from aryl diazonium salts were regioselectively installed at ortho position of iodoarenes via palladium catalyzed C−H activation. Mechanistic studies showed that, in contrast to classical Pd0−PdII−PdIV−PdII−Pd0 catalytic cycle, this radical cascades performed

  开发了碘芳烃与芳基重氮盐的Cu/Pd 共催化 Catellani 型邻位芳基化反应。衍生自芳基重氮盐的芳基通过钯催化的 CH 活化区域选择性地安装在碘芳烃的邻位。机理研究表明，与经典的Pd 0 -Pd II -Pd IV -Pd II -Pd 0催化循环相反，这种自由基级联通过Pd 0 -Pd II -Pd III -Pd I -Pd 0 循环进行。
• Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters
  作者：Zahid Hassan、Munawar Hussain、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tet.2012.05.026

  日期：2012.8

  Chemoselective Suzuki-Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the triflate group is electronically more deficient by the presence of a neighbouring acetyl group. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 1,2-Diarylnaphthalenes by Chemoselective Suzuki-Miyaura Reactions of 2-Bromo-1-(trifluoromethanesulfonyloxy)naphthalene
  作者：Peter Langer、Zahid Hassan、Munawar Hussain

  DOI：10.1055/s-0030-1260955

  日期：2011.8

  Suzuki-Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, readily available from 1-tetralone in two steps, afforded a variety of 1,2-diarylnaphthalenes. The reactions proceed with excellent chemoselectivity in favor of the bromide position, while the triflate remained unattacked.

  通过Suzuki-Miyaura反应，以1-四氢萘酮为原料经过两步制备的2-溴-1-(三氟甲烷磺酰氧)萘，可得到多种1,2-二芳基萘。反应具有极佳的化学选择性，优先发生溴位取代，而三氟甲烷磺酰氧基保持未反应状态。