(Z)-3-Bromo-4-(4-methoxy-phenyl)-2-oxo-but-3-enoic acid methyl ester | 42393-23-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-3-Bromo-4-(4-methoxy-phenyl)-2-oxo-but-3-enoic acid methyl ester
• CAS: 42393-23-7
• 化学式: C₁₂H₁₁BrO₄
• 分子量: 299.121
• InChiKey: QILIMMURMHVIMK-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-Bromo-4-(4-methoxy-phenyl)-2-oxo-but-3-enoic acid methyl ester 在 sodium tetrahydroborate 作用下， 生成 (Z)-3-Bromo-4-(4-methoxy-phenyl)-but-3-ene-1,2-diol
  参考文献：
  名称：

  High yield endoselective heterocycloadditions involving benzylidenepyruvic esters as the heterodiene and an alkoxystyrene as the dienophile

  摘要：

  The benzylidenepyruvic esters 6, 10a-d and 11 smoothly reacted with the alkoxystyrenes 12 and 13 in refluxing hexane or toluene and in the presence of catalytic amounts of Eu(fod)(3), thus selectively lending to the endo adducts 14-21 in high yields. This represents the first examples of an efficient heterocycloaddition of styrene derivatives without using the high pressure technique. The above adducts are potential intermediates for sugiresinol 7 and related tetrahydropyran neolignans.

  DOI：

  10.1016/s0040-4039(00)78452-8
• 作为产物：
  描述：

  4-(4-甲氧基苯基)-2-氧代-3-丁烯酸甲酯 在 吡啶 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以74%的产率得到(Z)-3-Bromo-4-(4-methoxy-phenyl)-2-oxo-but-3-enoic acid methyl ester
  参考文献：
  名称：

  High yield endoselective heterocycloadditions involving benzylidenepyruvic esters as the heterodiene and an alkoxystyrene as the dienophile

  摘要：

  The benzylidenepyruvic esters 6, 10a-d and 11 smoothly reacted with the alkoxystyrenes 12 and 13 in refluxing hexane or toluene and in the presence of catalytic amounts of Eu(fod)(3), thus selectively lending to the endo adducts 14-21 in high yields. This represents the first examples of an efficient heterocycloaddition of styrene derivatives without using the high pressure technique. The above adducts are potential intermediates for sugiresinol 7 and related tetrahydropyran neolignans.

  DOI：

  10.1016/s0040-4039(00)78452-8