1,3-dimethyl-2-(hydroxymethyl)-1-(4'-methoxy-4'-methylpentyl)cyclohex-3-ene | 140848-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dimethyl-2-(hydroxymethyl)-1-(4'-methoxy-4'-methylpentyl)cyclohex-3-ene
• 英文别名: 2,4-dimethyl-3-hydroxymethyl-4-(4-methoxy-4-methylpentyl)-cyclohex-1-ene；2-Cyclohexene-1-methanol, 6-(4-methoxy-4-methylpentyl)-2,6-dimethyl-；[6-(4-methoxy-4-methylpentyl)-2,6-dimethylcyclohex-2-en-1-yl]methanol
• CAS: 140848-06-2
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: NAIQPKWJQXZODZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 反式,反式-金合欢醇 在 氟磺酸 作用下， 生成 (-)-补身醇 、 1,3-dimethyl-2-(hydroxymethyl)-1-(4'-methoxy-4'-methylpentyl)cyclohex-3-ene
  参考文献：
  名称：

  Polovinka, M. P.; Unzur, N. D.; Perutskii, V. B., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1871 - 1885

  摘要：

  DOI：

文献信息

• Cyclization and Rearrangements of Farnesol and Nerolidol Stereoisomers in Superacids
  作者：Marina P. Polovinka、Dina V. Korchagina、Yurii V. Gatilov、Irina Y. Bagrianskaya、Vladimir A. Barkhash、Victor B. Perutskii、Nikon D. Ungur、Pavel F. Vlad、Vladimir V. Shcherbukhin、Nikolai S. Zefirov

  DOI：10.1021/jo00085a044

  日期：1994.3

  Acid-catalyzed cyclization of 2,3-trans- and 2,3-cis-farensol proceeds regioselectively and stereospecifically, yielding drimenol and epi-drimenol, respectively. The trans and cis isomers of nerolidol undergo carbo- and heterocyclization reactions. The trans isomer gives tricyclic caged hydrocarbons with new skeletal types, while the rearrangements of the cis isomer produce derivatives of 2-oxabicyclo-[4.4.0]decane. The ICAR computer program was used to derive reasonable mechanisms for the acid-catalyzed transformations of nerolidol, and the probability of the mechanisms was evaluated by the molecular mechanics method.