bis-[3,3']-(1-methoxybuta-1,3-dienyl)methyl ether | 180388-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis-[3,3']-(1-methoxybuta-1,3-dienyl)methyl ether
• 英文别名: (1E)-1-methoxy-3-[[(E)-4-methoxy-2-methylidenebut-3-enoxy]methyl]buta-1,3-diene
• CAS: 180388-48-1
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: GTVGFIXKOSCSAJ-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 bis-[3,3']-(1-methoxybuta-1,3-dienyl)methyl ether 在 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以83%的产率得到bis-[3,3']-(N-methyl-(7,9-dioxo-5-methoxy)-8-azabicyclo[4.3.0]non-3-enyl)methyl 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
• 作为产物：
  描述：

  4-chloro-3-methylbut-2-enal dimethylacetal 在 sodium hydroxide 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 bis-[3,3']-(1-methoxybuta-1,3-dienyl)methyl ether
  参考文献：
  名称：

  1,4-Dialkoxy 1,3-dienes and bis(dienes)–stereocontrolled synthesis and reactivity

  摘要：

  gamma-Aryloxy and -alkoxy alpha,beta-unsaturated dimethyl acetals are direct precursors to (1Z, 3E)-1,4-dialkoxy 1,3-dienes and bis(dienes) which are fine partners in cycloaddition reactions with classical dienophiles.

  DOI：

  10.1039/cc9960001295