all-cis-2,4,6-trimethylcyclohexanol | 110444-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: all-cis-2,4,6-trimethylcyclohexanol
• CAS: 110444-36-5
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: XUKYNHXGHASYPE-SPJNRGJMSA-N

物化性质

• 沸点：
  183.0±0.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  10.0
• 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：

  all-cis-2,4,6-trimethylcyclohexanol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 生成 (2R,4r,6S)-2,4,6-trimethylcyclohexanone
  参考文献：
  名称：

  4,6,8,10,16-Penta- and 4,6,8,10,16,18-Hexamethyldocosanes from the Cane Beetle Antitrogus parvulus - Cuticular Hydrocarbons with Unprecedented Structure and Stereochemistry

  摘要：

  [GRAPHICS]The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus were deduced to be 4,6,8,10,16,18-hexa- and 4,6,8,10,16-pentamethyldocosanes 2 and 3, respectively. Isomers of 2,4,6,8-tetramethylundecanal 27, 36, and 37, derived from 2,4,6-trimethylphenol, were coupled with the phosphoranes 28 and 29 to furnish alkenes and, by reduction, diastereomers of 2 and 3. Chromatographic and spectroscopic comparisons confirmed 2 as either 6a or 6b and 3 as either 34a or 34b.

  DOI：

  10.1021/ol0361453
• 作为产物：
  描述：

  2,4,6-三甲酚 在 Rh on carbon 氢气 作用下， 反应 72.0h， 生成 all-cis-2,4,6-trimethylcyclohexanol
  参考文献：
  名称：

  4,6,8,10,16-Penta- and 4,6,8,10,16,18-Hexamethyldocosanes from the Cane Beetle Antitrogus parvulus - Cuticular Hydrocarbons with Unprecedented Structure and Stereochemistry

  摘要：

  [GRAPHICS]The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus were deduced to be 4,6,8,10,16,18-hexa- and 4,6,8,10,16-pentamethyldocosanes 2 and 3, respectively. Isomers of 2,4,6,8-tetramethylundecanal 27, 36, and 37, derived from 2,4,6-trimethylphenol, were coupled with the phosphoranes 28 and 29 to furnish alkenes and, by reduction, diastereomers of 2 and 3. Chromatographic and spectroscopic comparisons confirmed 2 as either 6a or 6b and 3 as either 34a or 34b.

  DOI：

  10.1021/ol0361453

文献信息

• Stereochemistry of lardolure
  作者：Kenji Mori、Shigefumi Kuwahara

  DOI：10.1016/s0040-4020(01)88158-8

  日期：1986.1
• Novel Cuticular Hydrocarbons from the Cane Beetle <i>Antitrogus parvulus</i>4,6,8,10,16-Penta- and 4,6,8,10,16,18-HexamethyldocosanesUnprecedented <i>anti-anti-anti</i>-Stereochemistry in the 4,6,8,10-Methyltetrad
  作者：Sharon Chow、Mary T. Fletcher、Lynette K. Lambert、Oliver P. Gallagher、Christopher J. Moore、Bronwen W. Cribb、Peter G. Allsopp、William Kitching

  DOI：10.1021/jo0481093

  日期：2005.3.1

  [GRAPHICS]The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus are 4,6,8,10,16-penta- and 4,6,8,10,16,18-hexamethyldocosanes, I and 2, respectively. Stereoisomers of 2,4,6,8-tetramethylundecanal of established relative stereochemistry were derived from 2,4,6-trimethylphenol and were then coupled with appropriate methyl-substituted phosphoranes 62 and 25 to furnish alkenes, which on reduction provided diastereomers of I and 2, respectively. Capillary gas chromatography, mass spectrometry, and high resolution C-13 NMR spectroscopy confirmed 1 as either 84a or 84b and 2 as either 15a or 15b. The novelty of these structures and their relative stereochemistry is briefly related to polyketide assembly.