4-(4-methoxyphenyl)-2,3-pentadienoic acid ethyl ester | 155096-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-methoxyphenyl)-2,3-pentadienoic acid ethyl ester
• CAS: 155096-11-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: OVQUDNIULOIMPE-UHFFFAOYSA-N

物化性质

• 沸点：
  375.3±22.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-2,3-pentadienoic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以1.05 g的产率得到4-(4-Methoxy-phenyl)-penta-2,3-dienoic acid
  参考文献：
  名称：

  Schmittel, Michael; Woehrle, Clemens; Bohn, Ingo, Chemistry - A European Journal, 1996, vol. 2, # 8, p. 1031 - 1040

  摘要：

  DOI：
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 1-异丙烯基-4-甲氧基苯 在 sodium hydride 作用下， 生成 4-(4-methoxyphenyl)-2,3-pentadienoic acid ethyl ester
  参考文献：
  名称：

  Cation Radical Catalyzed Diels-Alder Reaction of Electron-Rich Allenes

  摘要：

  The cation radical catalyzed cycloaddition of electron-rich arylallenes 1a-e with 1,2,3,4,5-pentamethylcyclopentadiene (2a) afforded the Diels-Alder products 3 and 4 at 0 degrees C in 5 min with a high chemoselectivity, facial selectivity, and stereoselectivity. From the results of various mechanistic tests, it is inferred that the electron transfer induced reaction proceeds via a [3 + 2] pathway by cycloaddition of the diene cation radical to a neutral allene 1 exhibiting a rather short chain length. However, with electron-withdrawing substituents at the remote end of the allene functionality, the cycloaddition is only a minor reaction path. With diarylallene 1f and diene 2a, or 2b, no cycloaddition but formation of products 7 and d(1)-7 occurred. It is concluded that distonic cation radicals may be intermediates in a stepwise formal Diels-Alder reaction induced by electron transfer.

  DOI：

  10.1021/jo00130a022

文献信息

• Cation Radical Catalyzed Diels-Alder Reaction of Electron-Rich Allenes
  作者：M. Schmittel、C. Woehrle

  DOI：10.1021/jo00130a022

  日期：1995.12

  The cation radical catalyzed cycloaddition of electron-rich arylallenes 1a-e with 1,2,3,4,5-pentamethylcyclopentadiene (2a) afforded the Diels-Alder products 3 and 4 at 0 degrees C in 5 min with a high chemoselectivity, facial selectivity, and stereoselectivity. From the results of various mechanistic tests, it is inferred that the electron transfer induced reaction proceeds via a [3 + 2] pathway by cycloaddition of the diene cation radical to a neutral allene 1 exhibiting a rather short chain length. However, with electron-withdrawing substituents at the remote end of the allene functionality, the cycloaddition is only a minor reaction path. With diarylallene 1f and diene 2a, or 2b, no cycloaddition but formation of products 7 and d(1)-7 occurred. It is concluded that distonic cation radicals may be intermediates in a stepwise formal Diels-Alder reaction induced by electron transfer.
• Schmittel, Michael; Woehrle, Clemens; Bohn, Ingo, Chemistry - A European Journal, 1996, vol. 2, # 8, p. 1031 - 1040
  作者：Schmittel, Michael、Woehrle, Clemens、Bohn, Ingo

  DOI：——

  日期：——