campholenic aldehyde dimethyl acetal

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: campholenic aldehyde dimethyl acetal
• 英文别名: (2,2,3-trimethyl-cyclopent-3-en-1-yl)-acetaldehyde dimethyl acetal；(4R)-4-(2,2-dimethoxyethyl)-1,5,5-trimethylcyclopentene
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: HKVDRKISWRYMIT-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 (-)-Alpha-氧化蒎烯 在 polystyrene-divinylbenzene imprinted with trans-carvyl amine 作用下， 反应 1.0h， 生成 (-)-trans-carveol 、 campholenic aldehyde dimethyl acetal 、 5-(1-methoxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enol 、 1,7,7-trimethyl-6-exo-methoxy-bicyclo[2.2.1]heptan-2-endo-ol
  参考文献：
  名称：

  A study of some molecularly imprinted polymers as protic catalysts for the isomerisation of α-pinene oxide to trans-carveol

  摘要：

  A range of acidic Molecularly Imprinted Polymers (MIPs) were synthesised using the imprint molecule trans-carvyl amine as a transition state analogue for the selective isomerisation of alpha-pinene oxide to trans-carveol. The amine functionality of the imprint molecule was used to selectively position a sulfonic acid group in the MIP binding pocket utilising 4-styrene sulfonic acid as the functional monomer. Co-polymerisation with varying ratios of styrene and divinylbenzene afforded a range of MIPs which were tested for their ability to effect selective formation of trans-carveol from alpha-pinene oxide. Although successful imprinting was demonstrated in binding studies, it was shown that solvent effects were dominant in effecting selective formation of trans-carveol. Using DMF as solvent, up to 70% of the products from acid catalysed isomerisation of alpha-pinene oxide with the polystyrene MIPs were obtained via the necessary para menthyl tertiary carbocation, and industrially important trans-carveol was obtained in 45% yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.016