2-甲氧基-6-(4-甲氧基苯基)萘 | 59115-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲氧基-6-(4-甲氧基苯基)萘
• 英文名称: 2-methoxy-6-(4-methoxyphenyl)naphthalene
• CAS: 59115-47-8
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: MNBOGGWWWXXYKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-甲氧基-6-(4-甲氧基苯基)萘 在 正丁基锂 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 2-methoxy-6-(4-methoxyphenyl)-1-fluoronaphthalene
  参考文献：
  名称：

  ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity

  摘要：

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

  DOI：

  10.1021/jm058173s
• 作为产物：
  描述：

  7-甲氧基-3-(4-甲氧基-苯基)-1,2,3,4-四氢-[1]萘酚 在 phosphorus pentoxide 、 四氯苯醌 、 xylene 、 苯 作用下， 生成 2-甲氧基-6-(4-甲氧基苯基)萘
  参考文献：
  名称：

  Cymerman-Craig et al., Australian Journal of Chemistry, 1956, vol. 9, p. 373,379

  摘要：

  DOI：

文献信息

• Substituted phenyl naphthalenes as estrogenic agents
  申请人：Wyeth

  公开号：US20030181519A1

  公开（公告）日：2003-09-25

  This invention provides estrogen receptor modulators of formula I, having the structure 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 , are as defined in the specification, or a pharmaceutically acceptable salt thereof.

  这项发明提供了具有结构的式I的雌激素受体调节剂 1 其中 R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 ，R 7 ，R 8 ，R 9 和R 10 如规范中所定义，或其药用可接受盐。
• Substituent Effects on the Iodine-Catalyzed Thermal Cyclization of 3,4-Diphenylbuta-1,3-dienyl Isocyanates: Mechanistic Studies
  作者：Ta-Hsien Chuang、Wei-Yu Chang、Chien-Fu Li、Yu-Chia Wen、Chia-Chen Tsai

  DOI：10.1021/jo2017247

  日期：2011.12.2

  The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates 1, generated in situ from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones 2, phenylnaphthalenes 3, and indenes 4 were produced via intramolecular ring closure. The nature of the substituents on the phenyl rings was found to be crucial to the distribution of cyclized products 2–4. The mechanism

  使用碘作为催化剂，研究了由相应的叠氮化物就地生成的3,4-二苯基丁-1,3-二烯基异氰酸酯1的热环化反应。经由分子内环闭合产生二苯基吡啶酮2，苯基萘3和茚满4。在苯环上具有取代基的性质被认为是到环化产物的分布至关重要2 - 4。还讨论了反应机理。
• Design, Synthesis, and Biological Evaluation of (Hydroxyphenyl)naphthalene and -quinoline Derivatives: Potent and Selective Nonsteroidal Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1) for the Treatment of Estrogen-Dependent Diseases
  作者：Martin Frotscher、Erika Ziegler、Sandrine Marchais-Oberwinkler、Patricia Kruchten、Alexander Neugebauer、Ludivine Fetzer、Christiane Scherer、Ursula Müller-Vieira、Josef Messinger、Hubert Thole、Rolf W. Hartmann

  DOI：10.1021/jm701447v

  日期：2008.4.1

  Human 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) catalyzes the reduction of the weak estrogen estrone (E1) to the highly potent estradiol (E2). This reaction takes place in the target cell where the estrogenic effect is exerted via the estrogen receptor (ER). Estrogens, especially E2, are known to stimulate the proliferation of hormone-dependent diseases. 17beta-HSD1 is overexpressed

  人类17β-羟基类固醇脱氢酶1（17beta-HSD1）催化将弱雌激素雌酮（E1）还原为强效雌二醇（E2）。该反应在靶细胞中发生，在靶细胞中通过雌激素受体（ER）发挥雌激素作用。已知雌激素，尤其是E2会刺激激素依赖性疾病的扩散。17beta-HSD1在许多乳腺肿瘤中过表达。因此，它是治疗这些疾病的有吸引力的靶标。基于配体和结构的药物设计导致发现17beta-HSD1的新型，选择性和有效抑制剂。合成了苯基取代的双环部分，作为类固醇底物的模拟物。使用计算方法来了解它们与蛋白质的相互作用。
• Ruthenium-Catalyzed Aromatization of Aromatic Enynes via the 1,2-Migration of Halo and Aryl Groups:  A New Process Involving Electrocyclization and Skeletal Rearrangement
  作者：Hung-Chin Shen、Sitaram Pal、Jian-Jou Lian、Rai-Shung Liu

  DOI：10.1021/ja0379159

  日期：2003.12.1

  The halo and aryl substituents of the 1,2-disubstituted styryl group of aromatic enynes undergo a 1,2-shift in the aromatization reaction catalyzed by TpRuPPh3(CH3CN)2PF6 (10 mol %) in toluene (110 degrees C, 6-8 h). The aryl group shifts to the neighboring olefin carbon, and the iodo (or bromo) substituent migrates to the terminal alkyne carbon. The mechanisms of these two migrations have been elucidated

  芳族烯炔的 1,2-二取代苯乙烯基的卤素和芳基取代基在由 TpRuPPh3(CH3CN)2PF6 (10 mol %) 催化的芳构化反应中发生 1,2-位移（110 摄氏度，6-8 度） H）。芳基转移到相邻的烯烃碳，碘（或溴）取代基转移到末端炔碳。同位素标记实验阐明了这两种迁移的机制。这表明 1,2-芳基位移来自钌-亚乙烯基物种的 5-endo-dig 电环化，而 1,2-iodo 位移遵循 6-endo-dig 途径。
• Methylation of arenes via Ni-catalyzed aryl C–O/F activation
  作者：Bing-Tao Guan、Shi-Kai Xiang、Tao Wu、Zuo-Peng Sun、Bi-Qin Wang、Ke-Qing Zhao、Zhang-Jie Shi

  DOI：10.1039/b718998b

  日期：——

  Aryl C–O and C–F can be transformed into C–Me viaNi-catalyzed coupling with MeMgBr under mild conditions.

  芳基C–O和C–F可以在温和条件下通过Ni催化与MeMgBr的耦合反应转化为C–Me。