methyl (Z)-4-(2-formylphenyloxy)but-2-enoate | 88018-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (Z)-4-(2-formylphenyloxy)but-2-enoate
• 英文别名: methyl (Z)-4-(2-formylphenoxy)but-2-enoate
• CAS: 88018-07-9
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: UDALHVUWSFOPSC-DAXSKMNVSA-N

物化性质

• 熔点：
  76-77 °C(Solv: ethanol (64-17-5))
• 沸点：
  367.2±27.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  6
• 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
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-4-(2-formylphenyloxy)but-2-enoate 反应 0.25h， 以15%的产率得到methyl (E)-4-(2-formylphenoxy)but-2-enoate
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074
• 作为产物：
  描述：

  顺丁烯二酸单甲酯 在 硼烷四氢呋喃络合物 、 potassium carbonate 、 三乙胺 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 methyl (Z)-4-(2-formylphenyloxy)but-2-enoate
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074

文献信息

• Preparation of Axially ChiralN,N′-Diarylimidazolium andN-Arylthiazolium Salts and Evaluation of Their Catalytic Potential in the Benzoin and in the Intramolecular Stetter Reactions
  作者：Jens Pesch、Klaus Harms、Thorsten Bach

  DOI：10.1002/ejoc.200300762

  日期：2004.5

  imidazolium salts 15b, the thiazolium salts proved to be suitable catalysts in the benzoin condensation of benzaldehyde (1 2) and in the intramolecular Stetter reaction of the α,β-unsaturated ester 9a. The best results obtained with catalyst 19 (20 mol %) were 85% yield of product 2 (40% ee) and 75% yield of product 10a (50% ee). The stereogenic axis of catalyst 19 is not configurationally stable in the

  制备了 N-芳基取代的咪唑 14b、15b 和噻唑 17-22、25，它们包含立体轴并且可以作为阻转异构体出现。咪唑鎓盐 15b 可以从 2-异丙基苯胺 (12b) 和双乙酰 (11) 分三步获得（产率 19%），而它们的叔丁基类似物的合成失败。内消旋异构体 meso-15b 占优势（dr = 90/10）。手性噻唑鎓盐 rac-17（产率 53%）和 rac-22（产率 49%）由 2-叔丁基苯胺 (12a) 分两步制备。从α-溴薄荷酮(23)和苯胺12a(总产率为27%)获得对映异构纯的噻唑鎓盐19。与咪唑鎓盐 15b 相比，噻唑鎓盐被证明是苯甲醛的安息香缩合 (1 2) 和 α,β-不饱和酯 9a 的分子内 Stetter 反应中的合适催化剂。使用催化剂 19 (20 mol%) 获得的最佳结果是产物 2 的 85% 产率 (40% ee) 和产物 10a 的 75% 产率 (50%