trans-4-methyl-4,5-bis(hydroxymethyl)cyclohexane | 82442-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-4-methyl-4,5-bis(hydroxymethyl)cyclohexane
• 英文别名: 1-methyl-trans-1,2-bishydroxymethylcyclohexane；[(1R,2R)-2-(hydroxymethyl)-2-methylcyclohexyl]methanol
• CAS: 82442-66-8
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: KUSRJYWNGMZVHU-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-4-methyl-4,5-bis(hydroxymethyl)cyclohexane 在 吡啶 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 8-methyl-trans-2-thiahydrindane
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403
• 作为产物：
  描述：

  diethyl 1-methyl-4-cyclohexene-trans-1,2-dicarboxylate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 26.0h， 生成 trans-4-methyl-4,5-bis(hydroxymethyl)cyclohexane
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403

文献信息

• Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols
  作者：Ignac J. Jakovac、H. Bruce Goodbrand、Kar P. Lok、J. Bryan Jones

  DOI：10.1021/ja00381a024

  日期：1982.8