2,6-dimethyl-1,5-di(2-methyl) propanoyl naphthalene | 132181-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dimethyl-1,5-di(2-methyl) propanoyl naphthalene
• 英文别名: 2,6-dimethyl-1,5-di-(2-methyl)-propanoylnaphthalene
• CAS: 132181-76-1
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: XMRBKKFSMOYKEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,6-二甲基萘 在 正丁基锂 、 溴 、 碘 、 铁粉 作用下， 以 四氯化碳 为溶剂， 反应 9.0h， 生成 2,6-dimethyl-1,5-di(2-methyl) propanoyl naphthalene
  参考文献：
  名称：

  Conformational studies by dynamic NMR. 42. Detection of meso and racemic conformers resulting from a chirality created by the restricted torsion of hindered carbonyls

  摘要：

  Aromatic derivatives containing two equivalent, sterically hindered, carbonyl groups can exist either as meso or as racemic (d, l) conformers, owing to the noncoplanarity of the Ar and RC = O moieties which creates two centers of chirality. Molecular Mechanics calculations (MM-2) carried out on 2,6-dimethyl-1,5-di(2-methyl)propanoylnaphthalene (1) suggest that the meso form is only 0.5 kcal mol-1 (1 kcal = 4.184 J) more stable than the racemic conformer. Solid-state nmr spectra on a bulk sample are not in contrast with the result of the X-ray analysis on a single crystal that the meso conformer is the only species which is present in the solid. On the other hand low-temperature nmr spectra showed that both meso and racemic conformers are present in solution (e.g., 57% and 43% in CD2Cl2 at -85-degrees), the corresponding interconversion barrier (as determined by line shape computer simulation) being 10.7 kcal mol-1.

  DOI：

  10.1007/bf01160657