6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one
• 英文别名: (6R)-6-(dibromomethyl)-6-methylcyclohexa-2,4-dien-1-one
• 化学式: C₈H₈Br₂O
• 分子量: 279.959
• InChiKey: JGKSOYGPJNPDMO-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one 在 溴 作用下， 以 氘代氯仿 为溶剂， 反应 1.0h， 以100%的产率得到(2R,3R,4S,5S,6R)-2-dibromomethyl-2-methyl-3,4,5,6-tetrabromocyclohexan-1-one
  参考文献：
  名称：

  Bromination of 6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one

  摘要：

  Bromination of 6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one (I) with molecular bromine was studied at different ratios of reactants and varied reaction time. A number of tri-, tetra-, penta-, and hexabromo derivatives was obtained, which were characterized by H-1, C-13, IR, UV spectroscopy and elemental analysis. The molecular structure of (2R,3R,4S,5S,6R)-2-dibromomethyl-2-methyl-3,4,5,6-tetrabromocyclohexan-1-one (V) was revealed using XRD. It was shown that 2-bromo-6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one (III) upon standing for six months at room temperature dimerized quantitatively via Diels-Alder reaction to form IX. Dimer IX was investigated by the methods of cyclic voltammetry (CVA) and rotating disk electrode (RDE) in a solution of DMF on glassy carbon electrode.

  DOI：

  10.1134/s1070363213100083

文献信息

• Bromination of 6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one
  作者：G. V. Gavrilova、D. P. Krut’ko、A. A. Moiseeva、A. V. Churakov、E. K. Beloglazkina

  DOI：10.1134/s1070363213100083

  日期：2013.10

  Bromination of 6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one (I) with molecular bromine was studied at different ratios of reactants and varied reaction time. A number of tri-, tetra-, penta-, and hexabromo derivatives was obtained, which were characterized by H-1, C-13, IR, UV spectroscopy and elemental analysis. The molecular structure of (2R,3R,4S,5S,6R)-2-dibromomethyl-2-methyl-3,4,5,6-tetrabromocyclohexan-1-one (V) was revealed using XRD. It was shown that 2-bromo-6-dibromomethyl-6-methylcyclohexyl-2,4-dien-1-one (III) upon standing for six months at room temperature dimerized quantitatively via Diels-Alder reaction to form IX. Dimer IX was investigated by the methods of cyclic voltammetry (CVA) and rotating disk electrode (RDE) in a solution of DMF on glassy carbon electrode.