(2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal | 1128085-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal
• CAS: 1128085-93-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: PNPFHEDOOJVQHN-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  柠檬醛 在 氧气 、 tetraphenylporphyrin 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal 、 (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal
  参考文献：
  名称：

  对某些天然单萜的氧化研究：柠檬醛，普来高酮和樟脑

  摘要：

  Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C-2=C-3 and C-6=C-7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C-2=C-3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5-methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl)cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.

  DOI：

  10.1134/s1070428008060067