bis-[1,1']-(4-methoxy-2-methyl)buta-1,3-dienyl ether | 180388-47-0

• 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-methoxy-2-methyl)buta-1,3-dienyl ether
• 英文别名: (1Z,3E)-4-methoxy-1-[(1Z,3E)-4-methoxy-2-methylbuta-1,3-dienoxy]-2-methylbuta-1,3-diene
• CAS: 180388-47-0
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: BURPGMYTWNZHRH-HRDGMQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  6
• 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：

  bis-[1,1']-(4-methoxy-2-methyl)buta-1,3-dienyl ether 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 bis-[2,2']-N-methyl-(7,9-dioxo-5-methoxy-3-methyl)-8-azabicyclo[4.3.0]non-3-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
• 作为产物：
  描述：

  4-chloro-3-methylbut-2-enal dimethylacetal 在 sodium hydroxide 、 正丁基锂 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 bis-[1,1']-(4-methoxy-2-methyl)buta-1,3-dienyl 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

文献信息

• Tandem Cycloadditions of Functionalized Bis-Dienes. An Orthogonal Route to New Dipseudoglycals
  作者：Anne Guillam、Loïc Toupet、Jacques Maddaluno

  DOI：10.1021/jo990852l

  日期：1999.12.1

  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.
• Intramolecular Reactivity of a Captodative Bis-Diene
  作者：Silvia Aime、Hassan Oulyadi、Jacques Maddaluno、Paolo Venturello

  DOI：10.1021/ol991000a

  日期：1999.11.1

  [GRAPHICS]A 1,1-captodative bis-diene (3) has been prepared from crotonaldehyde diethyl acetal through an elimination-metalation sequence. This compound has been reacted with electron-rich and electron-deficient dienophiles. Under both thermal and high-pressure conditions, no intermolecular reaction was observed, the fused (4) and bridged (5) intramolecular bicyclic adducts being recovered. The reduction of the central carbonyl group has led to the corresponding allylic alcohol which, in thermal cycloaddition conditions, also provides an intramolecular adduct that aromatizes in the medium.