(2E)-1,1,4-trimethoxybut-2-ene | 211872-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-1,1,4-trimethoxybut-2-ene
• 英文别名: (E)-1,1,4-trimethoxybut-2-ene
• CAS: 211872-99-0
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: QISPMSVTAGXUMU-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2E)-1,1,4-trimethoxybut-2-ene 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (1Z,3Z)-1,4-二甲氧基-1,3-丁二烯 、 (1Z, 3E)-1,4-dimethoxy-1,3-butadiene
  参考文献：
  名称：

  Stereocontrolled Synthesis and Cycloaddition of 1,4-Dialkoxy 1,3-Dienes

  摘要：

  An efficient and stereocontrolled access to 1(Z),3(E)-1,4-dialkoxybutadienes is described that relies on a base-induced conjugated elimination reaction on y-alkoxy or aryloxy a,a-unsaturated acetals. The dienes have then been applied in [4 + 2] cycloaddition reactions where they demonstrate a good thermal reactivity toward activated dienophiles. Despite the 1,4-competition between oxygenated groups, both regio- and endoselectivities are total. A set of experiments has led to the conclusion that the (1Z,3E) pattern is responsible for these high stereocontrols. Several chiral alkoxy dienes have also been prepared following the same route. Their thermal cycloaddition with N-methylmaleimide leads to corresponding adducts in good yields and with total endoselectivities, but modest diastereoisomeric excess.

  DOI：

  10.1021/jo980321h
• 作为产物：
  描述：

  sodium methylate 、 E-4-bromobut-2-enal dimethyl acetal 以 甲醇 为溶剂， 反应 4.0h， 以73%的产率得到(2E)-1,1,4-trimethoxybut-2-ene
  参考文献：
  名称：

  Stereocontrolled Synthesis and Cycloaddition of 1,4-Dialkoxy 1,3-Dienes

  摘要：

  An efficient and stereocontrolled access to 1(Z),3(E)-1,4-dialkoxybutadienes is described that relies on a base-induced conjugated elimination reaction on y-alkoxy or aryloxy a,a-unsaturated acetals. The dienes have then been applied in [4 + 2] cycloaddition reactions where they demonstrate a good thermal reactivity toward activated dienophiles. Despite the 1,4-competition between oxygenated groups, both regio- and endoselectivities are total. A set of experiments has led to the conclusion that the (1Z,3E) pattern is responsible for these high stereocontrols. Several chiral alkoxy dienes have also been prepared following the same route. Their thermal cycloaddition with N-methylmaleimide leads to corresponding adducts in good yields and with total endoselectivities, but modest diastereoisomeric excess.

  DOI：

  10.1021/jo980321h

文献信息

• Stereocontrolled Synthesis and Cycloaddition of 1,4-Dialkoxy 1,3-Dienes
  作者：Anne Guillam、Loïc Toupet、Jacques Maddaluno

  DOI：10.1021/jo980321h

  日期：1998.7.1

  An efficient and stereocontrolled access to 1(Z),3(E)-1,4-dialkoxybutadienes is described that relies on a base-induced conjugated elimination reaction on y-alkoxy or aryloxy a,a-unsaturated acetals. The dienes have then been applied in [4 + 2] cycloaddition reactions where they demonstrate a good thermal reactivity toward activated dienophiles. Despite the 1,4-competition between oxygenated groups, both regio- and endoselectivities are total. A set of experiments has led to the conclusion that the (1Z,3E) pattern is responsible for these high stereocontrols. Several chiral alkoxy dienes have also been prepared following the same route. Their thermal cycloaddition with N-methylmaleimide leads to corresponding adducts in good yields and with total endoselectivities, but modest diastereoisomeric excess.