-1-methylcyclohexanol | 157563-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: -1-methylcyclohexanol
• CAS: 157563-10-5
• 化学式: C₇H₁₄O
• 分子量: 116.166
• InChiKey: VTBOTOBFGSVRMA-SPBYTNOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  -1-methylcyclohexanol 在 potassium hydrogensulfate 、 溴 作用下， 以 氯仿 为溶剂， 生成 [甲基,环13C2]-1,2-二溴-1-甲基环己烷
  参考文献：
  名称：

  The thermal Aromatization of Methyl-1,3-cyclohexadienes - an important argument against commonly accepted sigmatropic 1,7-H-shift reactions

  摘要：

  It has been demonstrated that the methyl and ring C-atoms of methyl-1,3-cyclohexadienes interchange their positions intramolecularly during the thermal conversion to toluene at temperatures above 600-degrees-C in a quartz flow system. Gas phase pyrolysis of double C-13-labeled methyl-1,3-cyclohexadienes with C-13-labels for the primary and the tertiary C-atom gave definite C-13-distribution patterns in the aromatic ring systems of the formed toluene as well as benzene with far-reaching similarities. The NMR data of the [C-13(2)]toluene isotopomers definitely rule out that the observed integration of the methyl C-atom into the ring system proceeds via the hitherto well-established sequence: electrocyclic ring opening of the 5-methyl-1,3-cyclohexadiene to 1,3,5-heptatriene, its sigmatropic 1,7-H shift and ensuing recyclization of the 1,3,5-heptatriene to methyl-1,3-cyclohexadienes.

  DOI：

  10.1002/prac.19943360303
• 作为产物：
  描述：

  碘甲烷-13C 、 环己酮-1-¹³C 在 magnesium 作用下， 生成 -1-methylcyclohexanol
  参考文献：
  名称：

  The thermal Aromatization of Methyl-1,3-cyclohexadienes - an important argument against commonly accepted sigmatropic 1,7-H-shift reactions

  摘要：

  It has been demonstrated that the methyl and ring C-atoms of methyl-1,3-cyclohexadienes interchange their positions intramolecularly during the thermal conversion to toluene at temperatures above 600-degrees-C in a quartz flow system. Gas phase pyrolysis of double C-13-labeled methyl-1,3-cyclohexadienes with C-13-labels for the primary and the tertiary C-atom gave definite C-13-distribution patterns in the aromatic ring systems of the formed toluene as well as benzene with far-reaching similarities. The NMR data of the [C-13(2)]toluene isotopomers definitely rule out that the observed integration of the methyl C-atom into the ring system proceeds via the hitherto well-established sequence: electrocyclic ring opening of the 5-methyl-1,3-cyclohexadiene to 1,3,5-heptatriene, its sigmatropic 1,7-H shift and ensuing recyclization of the 1,3,5-heptatriene to methyl-1,3-cyclohexadienes.

  DOI：

  10.1002/prac.19943360303