1,2-di(2-naphthyl)benzene | 1332869-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-di(2-naphthyl)benzene
• 英文别名: 2,2'-(1,2-Phenylene)dinaphthalene；2-(2-naphthalen-2-ylphenyl)naphthalene
• CAS: 1332869-80-3
• 化学式: C₂₆H₁₈
• 分子量: 330.429
• InChiKey: HGRDONMGZKZAPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,2-di(2-naphthyl)benzene 在 iron(III) chloride 作用下， 以 硝基甲烷 为溶剂， 反应 22.0h， 以13%的产率得到naphtho[1,2-g]chrysene
  参考文献：
  名称：

  1,2-二芳基苯的氧化分子内 C-C 键形成反应：高度共轭双桥多环芳烃的合成

  摘要：

  1,2-二芳基苯的氧化反应诱导分子内 C-C 键的形成。研究的底物是通过逐步 Suzuki-Miyaura 偶联反应制备的，该反应在苯的邻位引入 2-萘基、2-蒽基和 2-芘基。随后与 FeCl3 的氧化反应在分子的内部区域诱导了氧化 C-C 键形成反应。与我们之前的观察结果形成鲜明对比的是，形成了两个 C-C 键。理论计算表明，C-C 键的形成需要双（阳离子自由基）和/或阳离子自由基物种的反应位置处的大自旋密度。获得的 π 扩展分子在吸收光谱中显示出红移。

  DOI：

  10.1055/a-1560-4791
• 作为产物：
  描述：

  2-萘硼酸 在 palladium diacetate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 1,2-di(2-naphthyl)benzene
  参考文献：
  名称：

  Double-coupling of dibromo arenes with aryltriolborates for synthesis of diaryl-substituted planar frameworks

  摘要：

  A new method for simple and practical synthesis of diaryl-substituted arenes using potassium aryltriolborates was developed. Double-cross-coupling of dibromo arenes with aryltriolborates was carried out in the presence of a palladium catalyst, such as Pd(OAc)(2), Pd(PPh3)(4) or Pd(OAc)(2)/BIPHEP. The use of CuCl (40 mol %) with a palladium catalyst was found to be highly effective to give diaryl-substituted aromatic compounds in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.083

文献信息

• Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by <i>in Situ</i> Crystallization
  作者：Tamae Seo、Koji Kubota、Hajime Ito

  DOI：10.1021/jacs.0c01739

  日期：2020.6.3

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity of the crystalline monoarylated products rela-tive to the liquid starting materials should be attributed predom-inantly to the low diffusion efficiency of the former in the re-action mixture, which results in

  在机械化学条件下，钯催化的液体无偏二溴芳烃的 Suzuki-Miyaura 交叉偶联反应选择性地提供单芳基化产物。结晶单芳基化产物相对于液体原料的较低反应性主要归因于前者在反应混合物中的低扩散效率，这导致选择性单芳基化。本研究揭示了一种新方法，该方法使用固体中的原位相变来设计通过传统的基于溶液的合成难以实现的选择性有机转化。
• Method for Producing Mono-Cross-Coupled Aromatic Compound Having Leaving Group
  申请人：National University Corporation Hokkaido University

  公开号：US20230150919A1

  公开（公告）日：2023-05-18

  Disclosed is a method for producing a mono-cross-coupled aromatic compound (3-1) having one less leaving group than an aromatic compound (1) having at least two leaving groups, the method comprising: preparing the aromatic compound (1) having at least two leaving groups; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic boronic acid (2-1), an aromatic amino compound (2-2), a diboronic acid ester (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the aromatic compound (1) having at least two leaving groups with the compound (2) in the presence of a palladium catalyst and a base, in the absence of a solvent.
• Double-coupling of dibromo arenes with aryltriolborates for synthesis of diaryl-substituted planar frameworks
  作者：Gao-Qiang Li、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1016/j.tet.2011.06.083

  日期：2011.9

  A new method for simple and practical synthesis of diaryl-substituted arenes using potassium aryltriolborates was developed. Double-cross-coupling of dibromo arenes with aryltriolborates was carried out in the presence of a palladium catalyst, such as Pd(OAc)(2), Pd(PPh3)(4) or Pd(OAc)(2)/BIPHEP. The use of CuCl (40 mol %) with a palladium catalyst was found to be highly effective to give diaryl-substituted aromatic compounds in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Oxidative Intramolecular C–C Bond Formation Reactions of 1,2-Diarylbenzenes: Syntheses of Highly Conjugated Double-Bridged Polycyclic Aromatic Hydrocarbons
  作者：Ken-ichi Sugiura、Md. Rafikul Islam、Tohru Nishinaga、Kazunori Hirabayashi、Toshio Shimizu

  DOI：10.1055/a-1560-4791

  日期：2022.1

  2-diarylbenzenes induce intramolecular C–C bond formation. The substrates studied were prepared by the stepwise Suzuki–Miyaura coupling reaction that introduced 2-naphthyl, 2-anthranyl, and 2-pyrenyl groups on the ortho-positions of benzene. The subsequent oxidation reaction with FeCl3 induced an oxidative C–C bond formation reaction in the interior regions of the molecules. In marked contrast to our previous

  1,2-二芳基苯的氧化反应诱导分子内 C-C 键的形成。研究的底物是通过逐步 Suzuki-Miyaura 偶联反应制备的，该反应在苯的邻位引入 2-萘基、2-蒽基和 2-芘基。随后与 FeCl3 的氧化反应在分子的内部区域诱导了氧化 C-C 键形成反应。与我们之前的观察结果形成鲜明对比的是，形成了两个 C-C 键。理论计算表明，C-C 键的形成需要双（阳离子自由基）和/或阳离子自由基物种的反应位置处的大自旋密度。获得的 π 扩展分子在吸收光谱中显示出红移。