2,4-dinitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate | 249938-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,4-dinitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate
• 英文别名: 2,4-dinitrophenyl (2E,4E)-5-(4-hydroxyphenyl)pentadienoate；(2,4-dinitrophenyl) (2E,4E)-5-(4-hydroxyphenyl)penta-2,4-dienoate
• CAS: 249938-84-9
• 化学式: C₁₇H₁₂N₂O₇
• 分子量: 356.291
• InChiKey: VUGIGXVXYZIRPM-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-dinitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 在 氢氧化钾 、 potassium chloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 、 苯酚,2,4-二硝基-,盐钾
  参考文献：
  名称：

  A New, “Elongated” Oxo Ketene Intermediate in the Dissociative Hydrolysis of 2,4-Dinitrophenyl (2E,4E)-5-(4‘-Hydroxyphenyl)pentadienoate

  摘要：

  Reactivity comparison, Arrhenius parameters, and trapping of the above-depicted unsaturated intermediate strongly suggest that the alkaline hydrolysis of the title ester follows a mechanism of the E1cB type. This is the first observation of the occurrence of a dissociative route in the hydrolysis of an acyl derivative with three pi-systems interposed between the hydroxyl group (the internal nucleophile upon ionization) and the reaction center. Comparison with the hydrolysis of 2,4-dinitrophenyl 4'-hydroxybenzoate shows that interposition of the vinylenic groups is beneficial to the dissociative route.

  DOI：

  10.1021/ol990796a
• 作为产物：
  描述：

  在 氢氟酸 作用下， 生成 2,4-dinitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate
  参考文献：
  名称：

  芳基（2E，4E）-5-（4'-羟基苯基）戊二烯酸酯的解离碱水解中存在伸长的对氧乙烯酮中间体

  摘要：

  具有酸性离去基团的标题酯的碱性水解遵循E1cB机理，该机理涉及“超扩展”对-氧代乙烯酮中间体的参与。对于2,4-二硝基苯基酯动力学数据的水解，活化参数和中间体的捕集清楚地表明，解离途径携带了反应通量。表观二阶速率常数与离去基团的pK（a）的布朗斯德图的破坏表明，对于pK（a）大于约6的酯，反应机理从E1cB变为B（Ac）2。

  DOI：

  10.1021/jo0008439

文献信息

• A New, “Elongated” Oxo Ketene Intermediate in the Dissociative Hydrolysis of 2,4-Dinitrophenyl (2<i>E</i>,4<i>E</i>)-5-(4‘-Hydroxyphenyl)pentadienoate
  作者：Giorgio Cevasco、Daniele Vigo、Sergio Thea

  DOI：10.1021/ol990796a

  日期：1999.10.1

  Reactivity comparison, Arrhenius parameters, and trapping of the above-depicted unsaturated intermediate strongly suggest that the alkaline hydrolysis of the title ester follows a mechanism of the E1cB type. This is the first observation of the occurrence of a dissociative route in the hydrolysis of an acyl derivative with three pi-systems interposed between the hydroxyl group (the internal nucleophile upon ionization) and the reaction center. Comparison with the hydrolysis of 2,4-dinitrophenyl 4'-hydroxybenzoate shows that interposition of the vinylenic groups is beneficial to the dissociative route.
• Occurrence of an Elongated <i>p</i>-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl (2<i>E</i>,4<i>E</i>)-5-(4‘-Hydroxyphenyl)pentadienoates
  作者：Giorgio Cevasco、Daniele Vigo、Sergio Thea

  DOI：10.1021/jo0008439

  日期：2000.11.1

  The alkaline hydrolysis of title esters possessing acidic leaving groups follows an E1cB mechanism involving the participation of an "extra extended" p-oxo ketene intermediate. For the hydrolysis of the 2,4-dinitrophenyl ester kinetic data, activation parameters and trapping of the intermediate clearly indicate that the dissociative pathway carries the reaction flux. Break in the Bronsted plot of the

  具有酸性离去基团的标题酯的碱性水解遵循E1cB机理，该机理涉及“超扩展”对-氧代乙烯酮中间体的参与。对于2,4-二硝基苯基酯动力学数据的水解，活化参数和中间体的捕集清楚地表明，解离途径携带了反应通量。表观二阶速率常数与离去基团的pK（a）的布朗斯德图的破坏表明，对于pK（a）大于约6的酯，反应机理从E1cB变为B（Ac）2。