2,4-二硝基苯基肉桂酸酯 | 144230-54-6

• 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
• 中文名称: 2,4-二硝基苯基肉桂酸酯
• 英文名称: 2,4-Dinitrophenyl cinnamate
• 英文别名: 2-Propenoic acid, 3-phenyl-, 2,4-dinitrophenyl ester, (E)-；(2,4-dinitrophenyl) (E)-3-phenylprop-2-enoate
• CAS: 144230-54-6
• 化学式: C₁₅H₁₀N₂O₆
• 分子量: 314.254
• InChiKey: HZRYLVGEMHFJOE-RMKNXTFCSA-N

物化性质

• 沸点：
  510.1±50.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-二硝基苯基肉桂酸酯 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2,4-二硝基酚 、 肉桂酸
  参考文献：
  名称：

  Participation of an Extended p-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl 4-Hydroxycinnamates

  摘要：

  The alkaline hydrolysis of 4-hydroxycinnamate esters of acidic phenols follows an E1cB mechanism and involves the participation of an ''extended'' p-oxo ketene intermediate. The apparent bimolecular rate constant (k(a)K(a)/K-W) for the hydrolysis of the 2,4-dinitrophenyl ester is some 2500-fold larger than that determined from the Hammett relationship for the B(Ac)2 alkaline hydrolysis of substituted 2,4-dinitrophenyl cinnamates. The positive value of the entropy of activation for the hydrolysis of 2,4-dinitrophenyl 4'-hydroxycinnamate and trapping experiments with nitrogen nucleophiles are consistent with the dissociative pathway. A change from a E1cB to a B(Ac)2 mechanism is expected for esters with leaving groups having pK(a) higher than ca. 6.7. The higher E1cB reactivity of 2,4-dinitrophenyl 4'-hydroxycinnamate compared to that of the corresponding 4'-hydroxybenzoate is due to the vinylene group that further favors the dissociative route, probably increasing the stability of the unsaturated intermediate.

  DOI：

  10.1021/jo00100a031
• 作为产物：
  描述：

  2,4-二硝基酚 、 3-苯基-2-丙烯酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 2,4-二硝基苯基肉桂酸酯
  参考文献：
  名称：

  Y取代的苯基X取代的肉桂酸酯和苯甲酸酯的氨解作用：非离去基团从苯甲酰基到肉桂酰基的修饰作用

  摘要：

  动力学研究报道了Y取代的苯基X取代的肉桂酸酯（1a - e和3a - g）和苯甲酸酯（2a - e和4a - g）与一系列脂环族仲胺在80 mol％H 2 O中的反应/ 20 mol％DMSO在25.0±0.1°C下。2,4-二硝基苯基X-取代的肉桂酸酯（1a - e）和苯甲酸酯（2a - e）与胺的反应产生线性的Yukawa-Tsuno图。的ρ X值是的反应小得多1A - ë比2a - e的要大。的距离效应和反应机理（即，用于协同机制的性质1A - ë）已被建议来负责小ρ X值。2,4-二硝基苯基X-取代的肉桂酸酯（1a，1c和1e）与胺反应的布朗斯台德图是弯曲的，其βnuc值从0.65降低到0.3-0.4。Y取代的苯基肉桂酸酯（3a - g）与吗啉的反应也产生弯曲的布朗斯台德图，而Y取代的苯基苯甲酸酯（4a− e）表现出线性布朗斯台德图。已经得出结论，对于肉桂酸酯（1a，1c，1e和3a

  DOI：

  10.1021/jo0705061

文献信息

• Diamine and acid anhydride
  申请人：Kanegafuchi Kagaku Kogyo Kabushiki Kaisha

  公开号：US20020019558A1

  公开（公告）日：2002-02-14

  The present invention provides a novel diamine and a novel acid anhydride which are applicable for a polyimide and includes a cinnamoyl group or a derived cinnamoyl group. The novel diamines and acid anhydrides have photo-reactivity and heat-reactivity inherent to the cinnamoyl group.

  本发明提供了一种新型二胺和一种新型酸酐，适用于聚酰亚胺，并包括一个肉桂酰基或衍生的肉桂酰基。这些新型二胺和酸酐具有与肉桂酰基固有的光反应性和热反应性。
• Associative and Dissociative Pathways in the Alkaline Hydrolysis of Aryl 2-Hydroxycinnamates
  作者：Giorgio Cevasco、Sergio Thea

  DOI：10.1021/jo00106a016

  日期：1995.1

  Aryl 2-hydroxycinnamate esters hydrolyze in alkaline solutions (20% dioxane-water v/v) obeying the rate law k(obs) = k(2) + k(b)[OH-]/(1 + a(H)/K-a), where K-a is the ionization constant of the hydroxy group of the ester and kb is the second-order rate constant for the attack of hydroxide ion on the ionized ester. Kinetic data and activation parameters for the hydrolysis of the 2,4-dinitrophenyl ester show that the mechanism giving rise to the k(a) term cannot be a simple B(Ac)2 type process and suggest the occurrence of a E1cB mechanism involving an ''extended'' o-oxoketene intermediate. The Bronsted plot of the apparent second-order rate constants (k(a)K(a)/k(w)) versus the pK of the leaving group indicates that the reaction mechanism changes from E1cB to B(Ac)2 for esters with leaving groups having pK higher than about 6.
• US6303742B1
  申请人：——

  公开号：US6303742B1

  公开（公告）日：2001-10-16
• US6689899B2
  申请人：——

  公开号：US6689899B2

  公开（公告）日：2004-02-10
• Participation of an Extended p-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl 4-Hydroxycinnamates
  作者：Giorgio Cevasco、Sergio Thea

  DOI：10.1021/jo00100a031

  日期：1994.10

  The alkaline hydrolysis of 4-hydroxycinnamate esters of acidic phenols follows an E1cB mechanism and involves the participation of an ''extended'' p-oxo ketene intermediate. The apparent bimolecular rate constant (k(a)K(a)/K-W) for the hydrolysis of the 2,4-dinitrophenyl ester is some 2500-fold larger than that determined from the Hammett relationship for the B(Ac)2 alkaline hydrolysis of substituted 2,4-dinitrophenyl cinnamates. The positive value of the entropy of activation for the hydrolysis of 2,4-dinitrophenyl 4'-hydroxycinnamate and trapping experiments with nitrogen nucleophiles are consistent with the dissociative pathway. A change from a E1cB to a B(Ac)2 mechanism is expected for esters with leaving groups having pK(a) higher than ca. 6.7. The higher E1cB reactivity of 2,4-dinitrophenyl 4'-hydroxycinnamate compared to that of the corresponding 4'-hydroxybenzoate is due to the vinylene group that further favors the dissociative route, probably increasing the stability of the unsaturated intermediate.