bis-[1,1']-(4-methoxy-2-methyl-5,5,6,6-tetracyano)cyclohex-2-enyl ether

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis-[1,1']-(4-methoxy-2-methyl-5,5,6,6-tetracyano)cyclohex-2-enyl ether
• 英文别名: (3S,6S)-6-methoxy-4-methyl-3-[(1S,4S)-5,5,6,6-tetracyano-4-methoxy-2-methylcyclohex-2-en-1-yl]oxycyclohex-4-ene-1,1,2,2-tetracarbonitrile
• 化学式: C₂₄H₁₈N₈O₃
• 分子量: 466.459
• InChiKey: SPQVUUMMYYSKRQ-MUGJNUQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  218
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  四氰基乙烯 、 bis-[1,1']-(4-methoxy-2-methyl)buta-1,3-dienyl ether 在 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以54%的产率得到bis-[1,1']-(4-methoxy-2-methyl-5,5,6,6-tetracyano)cyclohex-2-enyl ether
  参考文献：
  名称：

  Tandem Cycloadditions of Functionalized Bis-Dienes. An Orthogonal Route to New Dipseudoglycals

  摘要：

  A direct and stereocontrolled access to a new class of conjugated bis-dienes is presented that relies on a double conjugated-elimination reaction induced by the action of strong bases such as n-BuLi or KHMDS on bis-alpha,beta-unsaturated acetals. These bis-dienes undergo double [4 + 2] cycloadditions with activated dienophiles under thermal conditions. With methyl acrylate, the reaction is totally endo and regiocontrolled with respect to both dienes and exhibits up to 60% inter-ring diastereocontrol when performed under high pressure. Mixed adducts can also be obtained by adding successively two different dienophiles. Again, the endo and regiocontrols are total while the ring-to-ring diastereocontrol depends on reaction conditions but remain, most of the time, relatively low. Double hetero-Diels-Alder reactions have also been performed, yielding bicyclic skeletons of novel 4<->4' disaccharidic structures. Finally, the corresponding nonconjugated bis-dienes have also been evaluated in cycloadditions. They react at room temperature with NMM or diethyl ketomalonate to provide highly functionalized polycyclic structures in high yields.

  DOI：

  10.1021/jo990852l