7-isopropyl-5-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 7-isopropyl-5-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene
• 英文别名: 5-Methyl-7-propan-2-yl-2,3-dioxabicyclo[2.2.2]oct-5-ene
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: PAGUSKCEKZOQHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-isopropyl-5-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene 以 甲苯 为溶剂， 以32%的产率得到(-)-(1R,2S,4S,5R,7R)-5-isopropyl-1-methyl-3,8-dioxatricyclo[5.1.0.0^2,4]octane
  参考文献：
  名称：

  Comparative analysis of three Australian finger lime (Citrus australasica) cultivars: Identification of unique citrus chemotypes and new volatile molecules

  摘要：

  The volatile constituents of the peel of three cultivars of Australian finger lime (Citrus australasica) were investigated: Alstonville, Judy's Everbearing and Durham's Emerald. Both qualitative and quantitative GC-MS analyses were performed on their peel solvent extract. The results showed that the unique phenotypes of finger lime are also correlated to unique molecular compositions. Each cultivar revealed a different chemotype: limonene/sabinene for cv. Alstonville, limonene/citronellal/isomenthone for cv. Judy's Everbearing, and limonene/citronellal/ citronellol for cv. Durham's Emerald. To the best of our knowledge, these chemotypes have never been reported in any other citrus species. Furthermore, the amounts of some volatile constituents (gamma-terpinene, alpha-pinene, beta-pinene, citral), which are generally the major constituents besides limonene in lime species, were surprisingly low in the three cultivars. Comparative GC-MS analysis also showed that some volatile molecules tended to be specific to one cultivar and could therefore be considered as markers. Moreover six molecules were reported for the first time in a citrus extract and confirmed by synthesis. Heart-cutting enantioselective two-dimensional GC-MS was performed to determine the enantiomeric distribution of the major chiral constituents. The combined data on three finger lime cultivars gives evidence of their divergence from other citrus species. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.10.023
• 作为产物：
  描述：

  水芹烯 在 5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrin 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以67%的产率得到7-isopropyl-5-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  聚乙二醇支持的四羟基苯基卟啉：一种方便，可回收的光氧化反应催化剂。

  摘要：

  [反应：见正文]制备了一种新的聚乙二醇负载的卟啉，并研究了其在光氧化反应中作为促进剂的能力。PEG负载的催化剂表现出与非锚定敏化剂可比的高活性，并且易于通过过滤从反应混合物中除去。与聚合物结合的卟啉已循环使用六次，而不会损失化学和立体化学效率。

  DOI：

  10.1021/ol0267230