9-(3-methoxyphenyl)phenanthrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-(3-methoxyphenyl)phenanthrene
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: XQAWTTOJADDUII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-((3-methoxyphenyl)ethynyl)-1,1’-biphenyl 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到9-(3-methoxyphenyl)phenanthrene
  参考文献：
  名称：

  2炔基联芳基的Brønsted酸催化的碳环化

  摘要：

  邻炔基联芳基在催化量的布朗斯台德酸存在下反应，在温和的条件下以高收率得到菲。该转化的活性和选择性由二芳基炔基部分的取代模式决定。在嗜碳性路易斯和布朗斯台德酸催化的环异构化过程中，炔烃活化存在选择性变化。

  DOI：

  10.1002/adsc.201801526

文献信息

• A new route to π-extended polycyclic aromatic hydrocarbons via cross-dehydrogenative coupling
  作者：Farnaz Jafarpour、Mojgan Ayoubi-Chianeh、Masoumeh Abbasnia、Meysam Azizzade

  DOI：10.1039/c7cy01040k

  日期：——

  Palladium-catalyzed cross-dehydrogenative coupling of phenanthrenes with simple arenes is innovated. This protocol provides an opportunity for a waste–minimized construction of π-extended PAHs with high atomic efficiency under mild and ligand-free conditions.

  创新了钯与简单芳烃的钯催化交叉脱氢偶联。该协议为在温和且无配体的条件下以最小的原子效率高效地构建π扩展的PAH提供了机会。
• Proton Abstraction Mechanism for the Palladium-Catalyzed Intramolecular Arylation
  作者：Domingo García-Cuadrado、Ataualpa A. C. Braga、Feliu Maseras、Antonio M. Echavarren

  DOI：10.1021/ja056165v

  日期：2006.2.1

  Under the usual conditions, the Pd-catalyzed arylation does not involve an electrophilic aromatic substitution reaction. On the basis of DFT calculations, we propose a mechanism for the Pd-catalyzed arylation that involves a proton abstraction by a carbonate or related ligand and that provides a satisfactory explanation for the experimental data.

  在通常条件下，钯催化的芳基化不涉及亲电芳香取代反应。在 DFT 计算的基础上，我们提出了一种 Pd 催化芳基化的机制，该机制涉及碳酸盐或相关配体的质子提取，并为实验数据提供了令人满意的解释。
• Proton-Abstraction Mechanism in the Palladium-Catalyzed Intramolecular Arylation:  Substituent Effects
  作者：Domingo García-Cuadrado、Paula de Mendoza、Ataualpa A. C. Braga、Feliu Maseras、Antonio M. Echavarren

  DOI：10.1021/ja071034a

  日期：2007.5.1

  The regioselectivity observed in the intramolecular palladium-catalyzed arylation of substituted bromobenzyldiarylmethanes as well as theoretical results demonstrate that the Pd-catalyzed arylation proceeds by a mechanism involving a proton abstraction by the carbonate, or a related basic ligand. The reaction is facilitated by electron-withdrawing substituents on the aromatic ring, which is inconsistent

  在分子内钯催化的取代溴苄基二芳基甲烷的芳基化反应中观察到的区域选择性以及理论结果表明，Pd 催化的芳基化反应通过涉及碳酸酯或相关碱性配体提取质子的机制进行。芳香环上的吸电子取代基促进了反应，这与亲电芳香取代机制不一致。更重要的定向效应是由反应位点邻位的吸电子取代基发挥的。
• 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%.
• PHENOL AND PYRIDINOL DERIVATIVES AS PHARMACEUTICALS
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0532531A1

  公开（公告）日：1993-03-24