8-methoxy-1-naphthonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-methoxy-1-naphthonitrile
• 英文别名: 1-Cyano-8-methoxynaphthalene；8-methoxynaphthalene-1-carbonitrile
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: QDWKPSWUNDCNSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 氰基萘 在 sodium persulfate 、 palladium diacetate 作用下， 反应 24.0h， 以60%的产率得到8-methoxy-1-naphthonitrile
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Alkoxylation of Arylnitriles via sp² C–H Bond Activation Using Cyano as the Directing Group

  摘要：

  A Pd(OAc)(2)-catalyzed ortho-alkoxylation of arylnitrile was described. Using cyano as a directing group, the aromatic C-H bond can be functionalized efficiently to generate ortho-alkoxylated arylnitrile derivatives with moderate yields. The optimal reaction conditions were identified after examining various factors such as oxidant, solvent, and reaction temperature. The method was compatible to the arylnitriles with either electron-withdrawing or electron-donating groups.

  DOI：

  10.1021/jo301384r

文献信息

• Crystal Structures of 8-Methoxy- and 8-Nitronaphthonitrile; Intramolecular Nucleophile-electrophile Interactions
  作者：Garry Procter、Doyle Britton、Jack D. Dunitz

  DOI：10.1002/hlca.19810640211

  日期：1981.3.18

  The crystal structures of 8-methoxy-1-naphthonitrile and 8-nitro-1-naphthonitrile have been determined by X-ray analysis. The methoxynitrile molecule shows a distortion pattern that is essentially similar to that found previously in other 1,8-disubstituted naphthalenes with Nu…CO interactions; instead of non-planarity at the carbonyl C-atom there is bending at the the cyano C-atom. Crystals of the

  通过X射线分析确定了8-甲氧基-1-萘腈和8-硝基-1-萘腈的晶体结构。甲氧基腈分子显示出的畸变模式与以前在其他具有Nu…CO相互作用的1,8-二取代萘中发现的畸变模式基本相似。取代羰基C原子处的非平面性，氰基C原子处发生弯曲。腈的晶体包含两个结构独立的，不对称的分子。两者均显示氰基基团弯曲，O…CN距离短和硝基不对称，但程度不同。在任何给定的畸变量与亲核试剂-亲电子试剂相互作用的强度之间没有明确的相关性。
• Pd(OAc)₂-Catalyzed Alkoxylation of Arylnitriles via sp² C–H Bond Activation Using Cyano as the Directing Group
  作者：Wu Li、Peipei Sun

  DOI：10.1021/jo301384r

  日期：2012.9.21

  A Pd(OAc)(2)-catalyzed ortho-alkoxylation of arylnitrile was described. Using cyano as a directing group, the aromatic C-H bond can be functionalized efficiently to generate ortho-alkoxylated arylnitrile derivatives with moderate yields. The optimal reaction conditions were identified after examining various factors such as oxidant, solvent, and reaction temperature. The method was compatible to the arylnitriles with either electron-withdrawing or electron-donating groups.