3-硝基-6-乙酰氧基-2,6-二甲基辛-1,7-二烯 | 137679-08-4

• 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
• 中文名称: 3-硝基-6-乙酰氧基-2,6-二甲基辛-1,7-二烯
• 英文名称: 3-nitro-6-acetoxy-2,6-dimethylocta-1,7-diene
• 英文别名: (3,7-dimethyl-6-nitroocta-1,7-dien-3-yl) acetate
• CAS: 137679-08-4
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: QWBHEBNNBHNEBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-硝基-6-乙酰氧基-2,6-二甲基辛-1,7-二烯 在 potassium fluoride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 19.5h， 生成 cis-trans-3E/Z-(1-oximinopropyliden-2')-2-acetoxymethyl-1-methylcyclopentan-ol
  参考文献：
  名称：

  A novel approach to the synthesis of cyclopentanoids of the iridane series based on 3-nitro-6-acetoxy-2,6-dimethylocta-1,7-diene

  摘要：

  The intramolecular [3 + 2] reaction of the silylnitronic ester generated in situ from the title nitroolefin proceeds with full inversion of regioselectivity, characteristic for the cycloaddition of nitronates to monosubstituted alkenes, and serves as a novel method for the construction of the iridane monoterpenoid skeleton. The structure of the cycloadducts obtained was determined by spectral and chemical methods. Their desilylation unexpectedly gives the aldoximes, the formation of which is regarded as the result of an unprecendented allylic isomerization of the tertiary nitroso intermediate.

  DOI：

  10.1007/bf00869517
• 作为产物：
  描述：

  乙酸芳樟酯 在 溶剂黄146 、 sodium nitrite 作用下， 反应 2.0h， 以76%的产率得到3-硝基-6-乙酰氧基-2,6-二甲基辛-1,7-二烯
  参考文献：
  名称：

  A novel approach to the synthesis of cyclopentanoids of the iridane series based on 3-nitro-6-acetoxy-2,6-dimethylocta-1,7-diene

  摘要：

  The intramolecular [3 + 2] reaction of the silylnitronic ester generated in situ from the title nitroolefin proceeds with full inversion of regioselectivity, characteristic for the cycloaddition of nitronates to monosubstituted alkenes, and serves as a novel method for the construction of the iridane monoterpenoid skeleton. The structure of the cycloadducts obtained was determined by spectral and chemical methods. Their desilylation unexpectedly gives the aldoximes, the formation of which is regarded as the result of an unprecendented allylic isomerization of the tertiary nitroso intermediate.

  DOI：

  10.1007/bf00869517

文献信息

• First example of reversed regioselectivity of [3 + 2] cycloaddition of a nitrone ether to a monosubstituted olefin
  作者：A. V. Belyankin、V. V. Veselovskii、A. M. Moiseenkov

  DOI：10.1007/bf00963520

  日期：1991.10