1-(2-联苯基)萘 | 60178-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-联苯基)萘
• 英文名称: 1,2'-Biphenylyl-naphthalin
• 英文别名: Naphthylbiphenyl；1-(2-phenylphenyl)naphthalene
• CAS: 60178-84-9
• 化学式: C₂₂H₁₆
• 分子量: 280.369
• InChiKey: MXVLMYZRJAHEIS-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  408.3±20.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• 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-联苯基)萘 在 碘 作用下， 生成 苯并[G]屈
  参考文献：
  名称：

  Photolytic rearrangement and halogen-dependent photocylization of halophenylnaphthalenes. II

  摘要：

  DOI：

  10.1021/ja01050a020
• 作为产物：
  描述：

  1-溴代萘 、 2-联苯硼酸 在 Pd(CN(2,6-(2,6-(i-Pr)2C6H3)2C6H3))2 、 sodium t-butanolate 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以71%的产率得到1-(2-联苯基)萘
  参考文献：
  名称：

  Synthetic and Mechanistic Interrogation of Pd/Isocyanide-Catalyzed Cross-Coupling: π-Acidic Ligands Enable Self-Aggregating Monoligated Pd(0) Intermediates

  摘要：

  Despite the large number of judiciously designed ligands that have been exploited in palladium-catalyzed cross-coupling protocols, the incorporation of ligands bearing appreciable pi-acidic properties has remained significantly underexplored. Herein, we demonstrate that well-defined and low-coordinate Pd-0 complexes supported by m-terphenyl isocyanides function as competent catalysts for the Suzuki Miyaura cross-coupling of aryl bromides and arylboronic acids. Two-coordinate Pd(CNArDiPP2)(2) was active for the coupling of unhindered aryl bromides at room temperature in 2-propanol, while increasing the temperature to 60 degrees C allowed for the use of mono-or di-ortho-substituted aryl bromides. Oxidative addition of the aryl bromide was shown to proceed via a dissociative mechanism, implicating monoligated Pd(CNArDipp2) as the catalytically active intermediate. Attempts to access this fleeting species via activation of the Pd-II monoisocyanide PdCl(eta(3)-C3H5)(CNArDipp2) with alkoxide base yielded the dinuclear Pd-I species mu-C3H5(mu-O'Pr)[Pd(CNArDipp2)](2). Although dinuclear Pd-I complexes are often produced as off-cycle species when using complexes of the type PdCl(eta(3)-allyl)L as precatalysts, this represents the first time that the comproportionation product (mu-allyl)(mu-Cl)[PdL](2) has been observed to undergo nucleophilic substitution with alkoxide, despite the fact that activating conditions for these precatalysts typically employ alkoxide bases. Remarkably, this alkoxide complex can undergo, beta-hydride elimination with expulsion of acetone and propene to produce two equivalents of, catalytically active Pd(CNArDipp2), which can self-aggregate to yield the isolable tripalladium cluster Pd-3(eta(2)-Dipp-mu-CNArDipp2)(3). This cluster is catalytically competent for the Suzuki Miyaura reaction and functions as a formal source of monoligated Pd(CNArDipp2) in solution.

  DOI：

  10.1021/acs.organomet.7b00035

文献信息

• Platinum-catalysed diborylation of arynes: synthesis and reaction of 1,2-diborylarenes
  作者：Hiroto Yoshida、Kengo Okada、Shota Kawashima、Kenji Tanino、Joji Ohshita

  DOI：10.1039/b919407j

  日期：——

  Arynes are found to be facilely inserted into bis(pinacolato)diboron by using a platinum–isocyanide catalyst, affording diverse 1,2-diborylarenes, which can be converted into o-terphenyls via Suzuki–Miyaura coupling reaction.

  研究发现，使用铂-异氰化物催化剂可以轻松将烯插入双（松香酸酯）二硼化合物中，生成多种1,2-二硼基芳烃，这些化合物可以通过铃木-宫浦偶联反应转化为邻三联苯。
• Preparation and Conformational Properties of Several 1,8-Diarylnaphthalenes
  作者：Eiichi Ibuki、Shigeru Ozasa、Yasuhiro Fujioka、Hiroshi Mizutani

  DOI：10.1246/bcsj.55.845

  日期：1982.3

  spectral studies of the 1,8-diarylnaphthalenes indicated the presence of a face-to-face arrangement of aromatic rings in the peri-position. Two new 8,8′-diaryl-1,1′-binaphthyls, each having two sets of closely held parallel aromatic rings, were isolated as minor coupling products. Trans-trans conformations were proposed for them on the basis of their thermal behavior. Several nickel(II) complexes were found

  六种新的 1,8-二芳基萘，每个都具有紧密的平行芳环，在 N,N'-双（1-甲基）存在下，通过芳基碘化镁和 1,8-二碘萘的 Kharash 型格氏交叉偶联合成。 -3-氧代丁叉基）乙二胺镍（II）作为催化剂。其中，1,8-二(1-萘基)萘以顺式和反式旋转异构体的形式获得，这是由于1,8-位旋转受限。通过差示扫描量热法确认旋转异构体之间在加热至其熔点以上时的相互转化。1,8-二芳基萘的质子磁共振光谱研究表明，在邻位存在芳香环的面对面排列。两个新的 8,8'-二芳基-1,1'-联萘，每个都有两组紧密相连的平行芳环，被分离为次要的偶联产物。根据它们的热行为提出了反式-反式构象。发现几种镍 (II) 配合物是有效的催化剂...
• 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。
• Parameters Influencing the Photochemical Cyclodehydrochlorination (CDHC) Reaction
  作者：Anthony Jolly、Charles‐Émile Fecteau、Paul Andrew Johnson、Jean‐François Morin

  DOI：10.1002/cplu.202300677

  日期：——

  The parameters influencing the outcome of the photochemical cyclodehydrochlorination (CDHC) reaction, including the nature of the solvent, the concentration and the presence of functional groups on the chlorinated substrates have been studied.

  研究了影响光化学环脱氯化氢（CDHC）反应结果的参数，包括溶剂的性质、浓度和氯化底物上官能团的存在。
• Synthetic and Mechanistic Interrogation of Pd/Isocyanide-Catalyzed Cross-Coupling: π-Acidic Ligands Enable Self-Aggregating Monoligated Pd(0) Intermediates
  作者：Brandon R. Barnett、Liezel A. Labios、Julia M. Stauber、Curtis E. Moore、Arnold L. Rheingold、Joshua S. Figueroa

  DOI：10.1021/acs.organomet.7b00035

  日期：2017.2.27

  Despite the large number of judiciously designed ligands that have been exploited in palladium-catalyzed cross-coupling protocols, the incorporation of ligands bearing appreciable pi-acidic properties has remained significantly underexplored. Herein, we demonstrate that well-defined and low-coordinate Pd-0 complexes supported by m-terphenyl isocyanides function as competent catalysts for the Suzuki Miyaura cross-coupling of aryl bromides and arylboronic acids. Two-coordinate Pd(CNArDiPP2)(2) was active for the coupling of unhindered aryl bromides at room temperature in 2-propanol, while increasing the temperature to 60 degrees C allowed for the use of mono-or di-ortho-substituted aryl bromides. Oxidative addition of the aryl bromide was shown to proceed via a dissociative mechanism, implicating monoligated Pd(CNArDipp2) as the catalytically active intermediate. Attempts to access this fleeting species via activation of the Pd-II monoisocyanide PdCl(eta(3)-C3H5)(CNArDipp2) with alkoxide base yielded the dinuclear Pd-I species mu-C3H5(mu-O'Pr)[Pd(CNArDipp2)](2). Although dinuclear Pd-I complexes are often produced as off-cycle species when using complexes of the type PdCl(eta(3)-allyl)L as precatalysts, this represents the first time that the comproportionation product (mu-allyl)(mu-Cl)[PdL](2) has been observed to undergo nucleophilic substitution with alkoxide, despite the fact that activating conditions for these precatalysts typically employ alkoxide bases. Remarkably, this alkoxide complex can undergo, beta-hydride elimination with expulsion of acetone and propene to produce two equivalents of, catalytically active Pd(CNArDipp2), which can self-aggregate to yield the isolable tripalladium cluster Pd-3(eta(2)-Dipp-mu-CNArDipp2)(3). This cluster is catalytically competent for the Suzuki Miyaura reaction and functions as a formal source of monoligated Pd(CNArDipp2) in solution.