1,8-Bis(4-methoxyphenyl)naphthalin | 77256-11-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,8-Bis(4-methoxyphenyl)naphthalin
• 英文别名: 1,8-Bis(4-methoxyphenyl)naphthalene
• CAS: 77256-11-2
• 化学式: C₂₄H₂₀O₂
• 分子量: 340.422
• InChiKey: FRGALSHFGKJSRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-Bis(4-methoxyphenyl)naphthalin 在 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-(4-trifluoromethylsulfonyloxyphenyl)-8-(4-methoxyphenyl)naphthalene
  参考文献：
  名称：

  Through-Space Control of the Persistence of Photogenerated o-Quinonoid Intermediates in Naphthalenes Containing Cofacially Oriented Chromenes and Arenes

  摘要：

  Remarkable modulation of the persistence of the photogenerated colored o-quinonoid intermediates via a through-space interaction has been demonstrated in chromenes 1-4 based on 1,8-diarylnaphthalenes. Polar/pi interaction is shown to stabilize the closed form of 4 to such an extent that photoinduced coloration is virtually invisible, while the same stabilization in the opened form of 2 permits ready coloration with a long-lived o-quinonoid intermediate.

  DOI：

  10.1021/ol300449p
• 作为产物：
  描述：

  1,8-二氨基萘 在 盐酸 、 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 34.0h， 生成 1,8-Bis(4-methoxyphenyl)naphthalin
  参考文献：
  名称：

  Through-Space Control of the Persistence of Photogenerated o-Quinonoid Intermediates in Naphthalenes Containing Cofacially Oriented Chromenes and Arenes

  摘要：

  Remarkable modulation of the persistence of the photogenerated colored o-quinonoid intermediates via a through-space interaction has been demonstrated in chromenes 1-4 based on 1,8-diarylnaphthalenes. Polar/pi interaction is shown to stabilize the closed form of 4 to such an extent that photoinduced coloration is virtually invisible, while the same stabilization in the opened form of 2 permits ready coloration with a long-lived o-quinonoid intermediate.

  DOI：

  10.1021/ol300449p

文献信息

• Exploring the selectivity of the Suzuki–Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes
  作者：Carlos F.R.A.C. Lima、José E. Rodriguez-Borges、Luís M.N.B.F. Santos

  DOI：10.1016/j.tet.2010.11.081

  日期：2011.1

  A series of 1-arylnaphthalenes and 1,8-diarylnaphthalenes were synthesized by the Suzuki–Miyaura cross-coupling methodology showing significant differentiation in the yields and selectivity between aryl rings with electron donating (higher yields), and electron withdrawing substituents (lower yields). These results strongly support the relation between the nucleophilicity of the boronate complex and

  Suzuki-Miyaura交叉偶联方法合成了一系列1-芳基萘和1,8-二芳基萘，显示出在带电子给体（较高的产率）和吸电子取代基（较低的产率）的芳环之间，产率和选择性存在显着差异。 。这些结果强烈支持硼酸酯络合物的亲核性与其反应性之间的关系，并强调了重金属化步骤在该交叉偶联反应的总效率中的重要性。用非对称的1,8-二芳基萘获得的结果表明，与1,8-二溴萘的单芳基化相比，已芳基化的物种（1-芳基-8-溴萘的中间体）的芳基化更容易。
• Synthesis and Molecular Structure of Symmetrical 1,8-Diarylnaphthalenes
  作者：Grégory Pieters、Vincent Terrasson、Anne Gaucher、Damien Prim、Jerôme Marrot

  DOI：10.1002/ejoc.201000685

  日期：2010.10

  The synthesis of substituted 1,8-diarylnaphthalenes is reported. A bis-Suzuki coupling strategy starting from 1,8-di-bromonaphthalene provides a useful and general route to the 1,8-diarylnaphthalene scaffold. In this context, N-heterocyclic benzhydrylamine ligands, in combination with PdCl 2 , were found to form especially efficient catalytic systems. The syn/anti ratios were determined in solution

  报道了取代的 1,8-二芳基萘的合成。从 1,8-二溴萘开始的双 Suzuki 偶联策略为 1,8-二芳基萘支架提供了有用的通用途径。在这种情况下，发现 N-杂环二苯甲基胺配体与 PdCl 2 结合形成特别有效的催化体系。从它们的 1 H NMR光谱在溶液中确定顺/反比。六种新靶材的固态分子结构分析重点关注萘核的变形。观察到的平面性缺乏是由几个参数引起的，例如取代基的性质和数量、取代模式以及共面环之间的空间拥挤和 π 堆积。
• Pillared salicylaldehyde derivatives as building blocks for the design of cofacial salen-type ligands
  作者：Laurent Sabater、Regis Guillot、Ally Aukauloo

  DOI：10.1016/j.tetlet.2005.02.092

  日期：2005.4

  The syntheses of pillared salicylaldehyde derivatives on a naphthalene block are reported. These compounds can be considered as building blocks for the elaboration of cofacial salen-typed ligands. The X-ray structure of a dinuclear manganese(III) complex is described, supporting our strategy to build topologically controlled multinuclear metal complexes.

  据报道在萘嵌段上有柱撑的水杨醛衍生物的合成。这些化合物可以被认为是用于加工塞伦型配体的基础。描述了双核锰（III）配合物的X射线结构，支持了我们构建拓扑控制的多核金属配合物的策略。
• Leppkes, Reinhard; Voegtle, Fritz, Angewandte Chemie, 1981, vol. 93, # 4, p. 404 - 405
  作者：Leppkes, Reinhard、Voegtle, Fritz

  DOI：——

  日期：——
• Leppkes, Reinhard; Voegtle, Fritz, Chemische Berichte, 1983, vol. 116, # 1, p. 215 - 219
  作者：Leppkes, Reinhard、Voegtle, Fritz

  DOI：——

  日期：——