[(E)-4-methoxy-2-methylidenebut-3-enoxy]benzene | 211873-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(E)-4-methoxy-2-methylidenebut-3-enoxy]benzene
• CAS: 211873-06-2
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: MIUGWRAYQYEAKT-CMDGGOBGSA-N

物化性质

• 沸点：
  308.1±25.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(E)-4-methoxy-2-methylidenebut-3-enoxy]benzene 、 酮基丙二酸二乙酯 在 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以94%的产率得到6-methoxy-4-phenoxymethyl-3,6-dihydropyran-2,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Thermal/Hyperbaric Heterocycloaddition of 1,4-Dialkoxy-1,3-dienes:  The de novo (E,Z) Way to Sugars

  摘要：

  1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.

  DOI：

  10.1021/jo0204193
• 作为产物：
  描述：

  4-chloro-3-methylbut-2-enal dimethylacetal 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 68.0h， 生成 [(E)-4-methoxy-2-methylidenebut-3-enoxy]benzene
  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