1-(1-naphthalenyl)pyrene | 88812-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-(1-naphthalenyl)pyrene
• 英文别名: 1-(1-pyrenyl)naphthalene；1-(1-naphthyl)pyrene；Pyrenylnaphthalene；1-naphthalen-1-ylpyrene
• CAS: 88812-42-4
• 化学式: C₂₆H₁₆
• 分子量: 328.413
• InChiKey: AIFDLIVBHPFKQK-UHFFFAOYSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  518.7±25.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• 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：

  1-溴代萘 、 1-溴芘 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 叔丁基锂 、 indium(III) chloride 作用下， 以 正戊烷 、 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 以76%的产率得到1-(1-naphthalenyl)pyrene
  参考文献：
  名称：

  Synthesis and Characterization of Polyaromatic Compounds Using Tri(naphthyl)indium

  摘要：

  A variety of polyaromatic compounds beating 1- and 2-naphthyl groups were prepared from the reactions of corresponding halides with tri(1- and 2-naphthyl)indium in good to excellent yields. Thermal, photophysical and electrochemical behaviors of carbazoles having naphthyl groups were studied. They have shown to be promising host and hole transporting materials in organic electroluminescence due to their high thermal stability, electrochemical reversibility and wide band gap.

  DOI：

  10.1021/jo800438n

文献信息

• Synthesis of Axially Chiral 1,1′-Binaphthalenes by Palladium-Catalysed Cross-Coupling Reactions of Triorganoindium Reagents
  作者：Ángeles Mosquera、Miguel A. Pena、José Pérez Sestelo、Luis A. Sarandeses

  DOI：10.1002/ejoc.201300042

  日期：2013.5

  heterocyclic analogues can be efficiently prepared by palladium-catalysed cross-coupling reactions between tri(1-naphthyl)indium reagents and 1-halonaphthalenes and haloisoquinolines. The reactions were usually carried out in THF at 80 °C with a slight excess of the indium reagent (40 mol-%) and a low catalyst loading (4 mol-% Pd) to afford the cross-coupling products in good yields (45–99 %). The method allows

  通过钯催化的三（1-萘基）铟试剂与 1-卤代萘和卤代异喹啉之间的交叉偶联反应，可以有效地制备 1,1'-联萘和杂环类似物。反应通常在 80 °C 的 THF 中进行，铟试剂略过量（40 mol%）和低催化剂负载（4 mol% Pd），以良好的产率提供交叉偶联产物（45 –99%）。该方法允许合成空间位阻的 2-取代和 2,2'-二取代 1,1'-联萘和萘基异喹啉。此外，偶联反应可以对映选择性进行，并通过使用手性氨基磷烷二茂铁基配体 (R,S)-PPFA 获得最佳对映体过量。
• Wahl, Peter; Krieger, Claus; Schweitzer, Dieter, Chemische Berichte, 1984, vol. 117, # 1, p. 260 - 276
  作者：Wahl, Peter、Krieger, Claus、Schweitzer, Dieter、Staab, H. A.

  DOI：——

  日期：——
• WAHL, P.;KRIEGER, C.;SCHWEITZER, D.;STAAB, H. A., CHEM. BER., 1984, 117, N 1, 260-276
  作者：WAHL, P.、KRIEGER, C.、SCHWEITZER, D.、STAAB, H. A.

  DOI：——

  日期：——
• Synthesis and Characterization of Polyaromatic Compounds Using Tri(naphthyl)indium
  作者：Wonhyung Lee、Youngjin Kang、Phil Ho Lee

  DOI：10.1021/jo800438n

  日期：2008.6.1

  A variety of polyaromatic compounds beating 1- and 2-naphthyl groups were prepared from the reactions of corresponding halides with tri(1- and 2-naphthyl)indium in good to excellent yields. Thermal, photophysical and electrochemical behaviors of carbazoles having naphthyl groups were studied. They have shown to be promising host and hole transporting materials in organic electroluminescence due to their high thermal stability, electrochemical reversibility and wide band gap.