1-(8-bromo-1-naphthyl)-2,2-dimethyl-1-propanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(8-bromo-1-naphthyl)-2,2-dimethyl-1-propanone
• 英文别名: 1-(8-Bromonaphthalen-1-yl)-2,2-dimethylpropan-1-one；1-(8-bromonaphthalen-1-yl)-2,2-dimethylpropan-1-one
• 化学式: C₁₅H₁₅BrO
• 分子量: 291.187
• InChiKey: GMHJLMQUBFCLOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(8-bromo-1-naphthyl)-2,2-dimethyl-1-propanone 、 苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 以30%的产率得到2,2-dimethyl-1-(8-phenyl-1-naphthyl)-1-propanone
  参考文献：
  名称：

  Conformational Studies by Dynamic NMR. 74.¹ Stereomutations of the Conformational Enantiomers in Peri-Substituted 1-Acylnaphthalenes

  摘要：

  Naphthalenes bearing an acyl and a phenyl group in a peri relationship give rise to a pair of enantiomers in the temperature range where the rotations of the acyl group are slow. Such enantiomers were observed by means of low temperature NMR spectra in chiral environments. The barrier to rotation for the acyl substituents, that causes the interconversion of the enantiomers, was demonstrated to be lower than that for the phenyl group. In an appropriately synthesized derivative it was possible to measure the two barriers that were found equal to 10.4 and 15.9 kcal mol(-1), respectively. The barriers for the acyl group rotation increase regularly (from 9.5 to 13.2 kcal mol(-1)) with the increasing dimension of the RCO groups (R = Me, Et, Pr-i, Bu-t). When a bromine atom replaces the phenyl group, the enantiomerization barrier for the corresponding acyl derivatives increases significantly.

  DOI：

  10.1021/jo991853g
• 作为产物：
  描述：

  8-bromo-1-naphthoyl chloride 、 叔丁基锂 在 CuCN 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 以64%的产率得到1-(8-bromo-1-naphthyl)-2,2-dimethyl-1-propanone
  参考文献：
  名称：

  Conformational Studies by Dynamic NMR. 74.¹ Stereomutations of the Conformational Enantiomers in Peri-Substituted 1-Acylnaphthalenes

  摘要：

  Naphthalenes bearing an acyl and a phenyl group in a peri relationship give rise to a pair of enantiomers in the temperature range where the rotations of the acyl group are slow. Such enantiomers were observed by means of low temperature NMR spectra in chiral environments. The barrier to rotation for the acyl substituents, that causes the interconversion of the enantiomers, was demonstrated to be lower than that for the phenyl group. In an appropriately synthesized derivative it was possible to measure the two barriers that were found equal to 10.4 and 15.9 kcal mol(-1), respectively. The barriers for the acyl group rotation increase regularly (from 9.5 to 13.2 kcal mol(-1)) with the increasing dimension of the RCO groups (R = Me, Et, Pr-i, Bu-t). When a bromine atom replaces the phenyl group, the enantiomerization barrier for the corresponding acyl derivatives increases significantly.

  DOI：

  10.1021/jo991853g

文献信息

• Conformational Studies by Dynamic NMR. 74.¹ Stereomutations of the Conformational Enantiomers in Peri-Substituted 1-Acylnaphthalenes
  作者：Lodovico Lunazzi、Andrea Mazzanti、Anna Muñoz Álvarez

  DOI：10.1021/jo991853g

  日期：2000.5.1

  Naphthalenes bearing an acyl and a phenyl group in a peri relationship give rise to a pair of enantiomers in the temperature range where the rotations of the acyl group are slow. Such enantiomers were observed by means of low temperature NMR spectra in chiral environments. The barrier to rotation for the acyl substituents, that causes the interconversion of the enantiomers, was demonstrated to be lower than that for the phenyl group. In an appropriately synthesized derivative it was possible to measure the two barriers that were found equal to 10.4 and 15.9 kcal mol(-1), respectively. The barriers for the acyl group rotation increase regularly (from 9.5 to 13.2 kcal mol(-1)) with the increasing dimension of the RCO groups (R = Me, Et, Pr-i, Bu-t). When a bromine atom replaces the phenyl group, the enantiomerization barrier for the corresponding acyl derivatives increases significantly.