2,4-Dinitrophenyl 4'-hydroxycinnamate | 144203-13-4

• 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: 2,4-Dinitrophenyl 4'-hydroxycinnamate
• 英文别名: 2,4-dinitrophenyl 4-hydroxycinnamate；(2,4-dinitrophenyl) (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 144203-13-4
• 化学式: C₁₅H₁₀N₂O₇
• 分子量: 330.254
• InChiKey: ULLIMVGRMDQXDB-FPYGCLRLSA-N

物化性质

• 沸点：
  557.0±50.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 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：
  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 4'-hydroxycinnamate 在 pH = 8.44 作用下， 以 水 、 丙酮 为溶剂， 29.0 ℃ 、100.0 kPa 条件下， 生成 2,4-二硝基酚 、 4-香豆酸
  参考文献：
  名称：

  酯水解的E 1cb路线；激活量是机制的附加标准

  摘要：

  原则上，在α或乙烯基位置具有酸性质子的酯的水解可以通过酮类中间体通过E 1cb途径进行水解。对于这种在4-羟基苯甲酸酯，丙二酸酯，乙酰乙酸酯和芴羧酸酯水解中的机理的动力学证据，现在增加了活化体积的进一步标准。Δ的值V ‡为反应由出发Ë 1CB路线是正和对比度与由更通常与水解相关的负值乙AC 2机构。

  DOI：

  10.1039/p29880000557

文献信息

• 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.
• Cevasco, Giorgio; Thea, Sergio, Gazzetta Chimica Italiana, 1992, vol. 122, # 5-7, p. 199 - 200
  作者：Cevasco, Giorgio、Thea, Sergio

  DOI：——

  日期：——
• NOVEL PEROXIDASE SUBSTRATES AND THEIR USE IN CATALYZED REPORTER DEPOSITION
  申请人：PerkinElmer LAS, Inc.

  公开号：EP1084269B1

  公开（公告）日：2007-04-25
• The E1cb route for ester hydrolysis; volumes of activation as an additional criterion of mechanism
  作者：Neil S. Isaacs、Tariq S. Najem

  DOI：10.1039/p29880000557

  日期：——

  of esters which possess an acidic proton at the α or vinylogous position can, in principle, hydrolyse by the E1cb route via a ketenoid intermediate. To the kinetic evidence for such a mechanism in the hydrolyses of 4-hydroxybenzoates, malonates, acetoacetates and fluorenecarboxylates is now added the further criterion of volumes of activation. Values of ΔV‡ for reactions proceeding by the E1cb route

  原则上，在α或乙烯基位置具有酸性质子的酯的水解可以通过酮类中间体通过E 1cb途径进行水解。对于这种在4-羟基苯甲酸酯，丙二酸酯，乙酰乙酸酯和芴羧酸酯水解中的机理的动力学证据，现在增加了活化体积的进一步标准。Δ的值V ‡为反应由出发Ë 1CB路线是正和对比度与由更通常与水解相关的负值乙AC 2机构。