cis-1-methyl-1,2-bis(hydroxymethyl)cyclohexane | 82442-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1-methyl-1,2-bis(hydroxymethyl)cyclohexane
• 英文别名: 1-methyl-cis-1,2-bishydroxymethylcyclohexane；[(1S,2R)-2-(hydroxymethyl)-2-methylcyclohexyl]methanol
• CAS: 82442-67-9
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: KUSRJYWNGMZVHU-BDAKNGLRSA-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：

  cis-1-methyl-1,2-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-cis-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：

  1-methyl-cis-4-cyclohexene-1,2-dicarboxylic anhydride 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 为溶剂， 反应 25.0h， 生成 cis-1-methyl-1,2-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

• The stereoselective alkylation of cyclohexane-1,2-dicarboxylic acid mono-(−)-menthyl ester
  作者：Samantha J. Hulme、Paul R. Jenkins、John Fawcett、David R. Russell

  DOI：10.1016/s0040-4039(00)73535-0

  日期：1994.7

  The dianion of (1R),(2S)-cyclohexane-1,2-dicarboxylic acid mono-(−)-menthyl ester reacts with alkyl bromides and an iodide to give alkylation with selectivities ranging from 7:1 to 32:1, the configuration of one product has been proved by X-ray crystallography.

  （1 R），（2 S）-环己烷-1,2-二羧酸单-（-）-薄荷酯的二价阴离子与烷基溴和碘化物反应生成烷基化反应，选择性范围为7：1至32：1 ，一种产品的构型已通过X射线晶体学证明。
• Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C–H oxidation
  作者：Nugzar Ghavtadze、Ferdinand S. Melkonyan、Anton V. Gulevich、Chunhui Huang、Vladimir Gevorgyan

  DOI：10.1038/nchem.1841

  日期：2014.2

  because of their abundance and low cost. Here we describe the conversion of 1-alkenes into 1,4-diols. The method involves the installation of a new Si,N-type chelating auxiliary group on the alkene followed by iridium-catalysed C–H silylation of an unactivated δ-C(sp3)–H bond to produce a silolane intermediate. Oxidation of the C–Si bonds affords a 1,4-diol. The method is demonstrated to have broad scope

  有机分子中 C-H 键无处不在的性质使它们作为快速生成复杂性的目标很有吸引力，但随之而来的是实现选择性反应的问题。在开发 C-H 功能化的新方法时，烯烃因其丰富和低成本而成为一种有吸引力的起始材料。在这里，我们描述了 1-烯烃转化为 1,4-二醇的过程。该方法包括在烯烃上安装新的 Si,N 型螯合辅助基团，然后在铱催化下对未活化的 δ-C（sp 3)–H 键生成硅酮中间体。C-Si 键的氧化得到 1,4-二醇。该方法适用于多种天然产物和衍生物的选择性 1,4-氧化，证明该方法具有广泛的适用范围和良好的官能团兼容性。
• 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