4-Cyanophenyl 2'-hydroxycinnamate | 159534-38-0

• 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: 4-Cyanophenyl 2'-hydroxycinnamate
• 英文别名: (4-cyanophenyl) (E)-3-(2-hydroxyphenyl)prop-2-enoate
• CAS: 159534-38-0
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: OAYSZJWASHNGSO-JXMROGBWSA-N

物化性质

• 沸点：
  491.8±38.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 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：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Cyanophenyl 2'-hydroxycinnamate 在 aq. alkali 作用下， 以 1,4-二氧六环 为溶剂， 生成 反式-2-羟基肉桂酸 、 4-羟基苯甲腈
  参考文献：
  名称：

  Associative and Dissociative Pathways in the Alkaline Hydrolysis of Aryl 2-Hydroxycinnamates

  摘要：

  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.

  DOI：

  10.1021/jo00106a016
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 在 草酰氯 、 氢氟酸 、 N,N-二甲基甲酰胺 作用下， 生成 4-Cyanophenyl 2'-hydroxycinnamate
  参考文献：
  名称：

  Associative and Dissociative Pathways in the Alkaline Hydrolysis of Aryl 2-Hydroxycinnamates

  摘要：

  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.

  DOI：

  10.1021/jo00106a016

文献信息

• 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.