4,5-Dicarbomethoxy-2,3,4,4a,5a,5,6,7-octahydrophenanthrene-3,4,5,6-tetracarboxylic Acid Dianhydride | 134815-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 4,5-Dicarbomethoxy-2,3,4,4a,5a,5,6,7-octahydrophenanthrene-3,4,5,6-tetracarboxylic Acid Dianhydride
• 英文别名: Dimethyl 4,6,17,19-tetraoxo-5,18-dioxapentacyclo[11.7.0.02,10.03,7.016,20]icosa-9,11,13-triene-3,20-dicarboxylate
• CAS: 134815-54-6
• 化学式: C₂₂H₁₈O₁₀
• 分子量: 442.379
• InChiKey: IUCYABFEGOZERA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  对二乙烯苯 、 (carbomethoxy)maleic anhydride 以 乙腈 为溶剂， 以55%的产率得到4,5-Dicarbomethoxy-2,3,4,4a,5a,5,6,7-octahydrophenanthrene-3,4,5,6-tetracarboxylic Acid Dianhydride
  参考文献：
  名称：

  Cycloaddition reactions of divinylbenzenes

  摘要：

  The reactions of m- and p-divinylbenzene with electrophilic olefins have been explored. In reactions with tetracyanoethylene (TCNE), m-divinylbenzene (m-DVB) is markedly more reactive than p-divinylbenzene (p-DVB). The reaction of m-DVB with TCNE leads to 2:1 Diels-Alder adduct 1, while the reaction of p-DVB with TCNE results in cyclobutane adduct 3. With maleic anhydride and alpha-carbomethoxymaleic anhydride, both m-DVB and p-DVB undergo double Diels-Alder reactions. The reactions of the para and meta isomers of diisopropenylbenzene (p-DIB and m-DIB) follow the same pattern. If p-DIB is mixed with methyl beta,beta-dicyanoacrylate (DCA), the reaction pathway can be changed from the [4 + 2] to the [2 + 2] cycloaddition by adding zinc chloride to increase the electrophilicity of DCA by complexing with the cyano substituents. The different pathways and reactivities are discussed.

  DOI：

  10.1021/jo00019a013