9-(4-biphenyl)phenanthrene | 95950-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-(4-biphenyl)phenanthrene
• 英文别名: 9-(Biphenylyl-(4))-phenanthren；9-(4-Phenylphenyl)phenanthrene
• CAS: 95950-75-7
• 化学式: C₂₆H₁₈
• 分子量: 330.429
• InChiKey: RAUDINPFZLMFHV-UHFFFAOYSA-N

物化性质

• 沸点：
  530.7±30.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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

• 作为产物：
  描述：

  联苯-4-丙烯酸 在 selenium 、 苦味酸 、 对苯二酚 作用下， 生成 9-(4-biphenyl)phenanthrene
  参考文献：
  名称：

  Skvarchenko,V.R. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 105 - 107

  摘要：

  DOI：

文献信息

• Metal-free cycloisomerizations of <i>o</i>-alkynylbiaryls
  作者：Jingyi Zhang、Siqi Li、Yan Qiao、Cheng Peng、Xiao-Na Wang、Junbiao Chang

  DOI：10.1039/c8cc05484c

  日期：——

  We describe a novel and highly efficient metal-free strategy to construct 9,9-disubstituted fluorenes and phenanthrenes via the TfOH-catalyzed cycloisomerizations of o-alkynylbiaryls. Notably, the significant effects of the electronic properties and steric hindrance of the alkyne terminus on the reaction selectivity have been observed.

  我们描述了一种新型且高效的无金属策略，可通过T-OH催化的邻炔基联芳基的环异构化反应来构建9,9-二取代的芴和菲。值得注意的是，已经观察到炔烃末端的电子性质和位阻对反应选择性的显着影响。
• Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes
  作者：Xiao Liu、Bingxin Zhou、Kelu Yan、Jiangwei Wen、Qiuyun Li、Xutong Wang、Xiu Wang

  DOI：10.1002/adsc.202301451

  日期：2024.4.23

  The transmetalation triggered rhodium‐catalyzed C‒H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium ylides has been developed. Various products of phenanthrenes were constructed under redox‐neutral conditions in 34−86% yields. Several mechanism exploration experiments and derivatization reactions were conducted in sequence to gain a deeper understanding

  已经开发出金属转移引发的铑催化的C-H键活化以及2-联苯硼酸与亚砜叶立德或碘叶立德的串联成环。在氧化还原中性条件下构建了各种菲产品，产率为 34-86%。依次进行了多次机制探索实验和衍生化反应，以更深入地了解这一转化的过程和潜力。它为菲衍生物的合成提供了一种替代方法。
• N-Heterocyclic-Carbene Complexes Readily Prepared from Di-μ-hydroxopalladacycles Catalyze the Suzuki Arylation of 9-Bromophenanthrene
  作者：J. Luis Serrano、José Pérez、Luis García、Gregorio Sánchez、Joaquín García、Pedro Lozano、Vidya Zende、Anant Kapdi

  DOI：10.1021/om501160n

  日期：2015.1.26

  New cyclometalated palladium complexes of general formula [Pd(Bmim)(X)(C boolean AND N)] have been synthesized by a novel reaction route involving di-mu-hydroxo-palladacycles [Pd(mu-OH)(C boolean AND N)}(2)] (C boolean AND N = 2-benzoylpyridine (Bzpy), I, previously unreported, or C boolean AND N = 2-phenylpyridine (Phpy), II)] and 1,3-butylmethylimidazolium salts [HBmim]X (X: Cl, Br, I, or saccharinate (Sacc); a, b, c, or d complexes, respectively). This simple acid-base reaction could not be achieved under identical conditions when corresponding di-mu-acetate complexes were used as starting materials. An alternative pathway to NHC/imidate complexes has also been explored by reacting IIb with [Ag(Phthal)(SMe2)](2) (Phthal = phthalimidate, e) to obtain [Pd(Bmim)(Phthal)(Phpy)], IIe. Structural characterization by X-ray diffraction of complexes Id, IIb, IId, and IIe has confirmed the proposed formulas. The mononuclear complexes have shown to catalyze the scalable Suzuki-Miyaura cross-coupling of 9-bromophenanthrene with a wide scope of aryl boronic acids, irrespective of their electronic properties and at a very low catalyst concentration of 0.01%.