1-(4-bromo-2,3-dimethyl-1-naphthyl)-1-ethanol | 210624-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-bromo-2,3-dimethyl-1-naphthyl)-1-ethanol
• 英文别名: 1-(4-Bromo-2,3-dimethylnaphthalen-1-yl)ethanol
• CAS: 210624-82-1
• 化学式: C₁₄H₁₅BrO
• 分子量: 279.176
• InChiKey: XNROQPDMKSVUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-bromo-2,3-dimethyl-1-naphthyl)-1-ethanol 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 1,4-diacetyl-2,3-dimethylnaphthalene
  参考文献：
  名称：

  Conformational Studies by Dynamic NMR. 65.¹ Interconversion of Stereolabile Meso and Racemic Diastereoisomers of Hindered 1,4-Diacylnaphthalenes

  摘要：

  1,4-Diacylnaphthalenes, bearing methyl groups in positions 2 and 3, display, at appropriate temperatures, NMR spectra due to meso and racemic stereolabile diastereoisomers, brought about by the restricted rotation of the two RCO substituents. As indicated by the diastereotopicity of appropriate prochiral substituents, these acyl groups are not coplanar to the naphthalene ring, and their C=O moieties can adopt either a syn or an anti arrangement. The meso (syn) and racemic (anti) structures were assigned, in solution, by taking into account the changes of their relative proportions in solvents of different polarity and, in the solid state, by X-ray diffraction. The free energies of activation for the interconversion were determined by computer line-shape simulation of the variable-temperature NMR spectra, and their values were found to increase substantially with the increasing bulkiness of the carbonyl-bonded alkyl groups (from 10.2 to 22.1 kcal mol-l for R = Me and R = t-Bu, respectively).

  DOI：

  10.1021/jo980149h
• 作为产物：
  描述：

  1,4-二溴-2,3-二甲基萘 、 乙醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到1-(4-bromo-2,3-dimethyl-1-naphthyl)-1-ethanol
  参考文献：
  名称：

  Conformational Studies by Dynamic NMR. 65.¹ Interconversion of Stereolabile Meso and Racemic Diastereoisomers of Hindered 1,4-Diacylnaphthalenes

  摘要：

  1,4-Diacylnaphthalenes, bearing methyl groups in positions 2 and 3, display, at appropriate temperatures, NMR spectra due to meso and racemic stereolabile diastereoisomers, brought about by the restricted rotation of the two RCO substituents. As indicated by the diastereotopicity of appropriate prochiral substituents, these acyl groups are not coplanar to the naphthalene ring, and their C=O moieties can adopt either a syn or an anti arrangement. The meso (syn) and racemic (anti) structures were assigned, in solution, by taking into account the changes of their relative proportions in solvents of different polarity and, in the solid state, by X-ray diffraction. The free energies of activation for the interconversion were determined by computer line-shape simulation of the variable-temperature NMR spectra, and their values were found to increase substantially with the increasing bulkiness of the carbonyl-bonded alkyl groups (from 10.2 to 22.1 kcal mol-l for R = Me and R = t-Bu, respectively).

  DOI：

  10.1021/jo980149h