4-(8-methylnaphthalen-1-yl)benzaldehyde | 1355320-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(8-methylnaphthalen-1-yl)benzaldehyde
• CAS: 1355320-60-3
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: YYNGTGSXSBHGPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (8-溴-1-萘)甲醇 在 四(三苯基膦)钯 、 三氟化硼乙醚 、 sodium cyanoborohydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 4-(8-methylnaphthalen-1-yl)benzaldehyde
  参考文献：
  名称：

  Influence of Substituents on the Through-Space Shielding of Aromatic Rings

  摘要：

  A series of naphthalene derivatives, bearing a methyl group and a substituted phenyl ring in a 1,8-relationship, have been synthesized. The chemical shifts of the protons of the methyl group, which are pointed toward the shielding zone of the phenyl ring, were monitored as the phenyl substituents were varied. This work indicates that the shielding effect of the phenyl ring is not so severely altered by the substituents as to significantly influence the chemical shift of the methyl group. Nonetheless, within the small changes observed experimentally, there appears to be a tendency for electron-withdrawing X to shift the methyl signal downfield, whereas electron-donating X-groups cause a more upfield shift. Polarization and field effects are discussed as possible causes for this phenomenon. Chemical shifts computed for selected members of the series, using the recently published procedures of Rablen and Bally, are in agreement with the experimentally observed trends.

  DOI：

  10.1021/jo202203r

文献信息

• Influence of Substituents on the Through-Space Shielding of Aromatic Rings
  作者：Colin W. Anson、Dasan M. Thamattoor

  DOI：10.1021/jo202203r

  日期：2012.2.17

  A series of naphthalene derivatives, bearing a methyl group and a substituted phenyl ring in a 1,8-relationship, have been synthesized. The chemical shifts of the protons of the methyl group, which are pointed toward the shielding zone of the phenyl ring, were monitored as the phenyl substituents were varied. This work indicates that the shielding effect of the phenyl ring is not so severely altered by the substituents as to significantly influence the chemical shift of the methyl group. Nonetheless, within the small changes observed experimentally, there appears to be a tendency for electron-withdrawing X to shift the methyl signal downfield, whereas electron-donating X-groups cause a more upfield shift. Polarization and field effects are discussed as possible causes for this phenomenon. Chemical shifts computed for selected members of the series, using the recently published procedures of Rablen and Bally, are in agreement with the experimentally observed trends.