bis-[1,1']-(4,4-dimethoxy-2-methyl)but-2-enyl ether | 257887-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis-[1,1']-(4,4-dimethoxy-2-methyl)but-2-enyl ether
• 英文别名: 4-(4,4-dimethoxy-2-methylbut-2-enoxy)-1,1-dimethoxy-3-methylbut-2-ene
• CAS: 257887-20-0
• 化学式: C₁₄H₂₆O₅
• 分子量: 274.357
• InChiKey: FCNVIASDYWRTCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis-[1,1']-(4,4-dimethoxy-2-methyl)but-2-enyl ether 在 双(三甲基硅烷基)氨基钾 、 对苯二酚 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、1300.0 MPa 条件下， 反应 76.0h， 生成 bis-[1,1']-(4-methoxy-5-methoxycarbonyl-2-methyl)cyclohex-2-ene 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 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以93%的产率得到bis-[1,1']-(4,4-dimethoxy-2-methyl)but-2-enyl 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