3-(4-Oxopyridin-1-yl)propanal | 141375-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4-Oxopyridin-1-yl)propanal
• CAS: 141375-48-6
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: UOHOXFPNOYLRMD-UHFFFAOYSA-N

物化性质

• 沸点：
  269.5±40.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Oxopyridin-1-yl)propanal 在 hydroxide 水 作用下， 生成 4-hydroxypyridine 、 丙烯醛
  参考文献：
  名称：

  Rate-determining steps in Michael-type additions and E1cb reactions in aqueous solution

  摘要：

  Rates of equilibration of a series of 10 substituted pyridines and five Michael acceptors (CH2=CHZ, Z = CHO, COCH3, SO2CH3, CN, and CONH2) with the corresponding N(ZCH2CH2) pyridinium cations have been measured in aqueous solution at ionic strength 0.1 and 25-degrees-C. Analysis of the dependence of the pseudo-first-order rate constants for equilibration as a function of acceptor concentration and of pH allows the evaluation of the second-order rate constants (k(Nu)) for the nucleophilic attack of each of these pyridines upon each of these acceptors and also the second-order rate constants (k(OH)) for the hydroxide ion catalyzed E1cb elimination reaction which is the microscopic reverse of each of these Michael-type addition reactions. Bronsted-type plots for each of these processes as a function of the basicity of the substituted pyridine are concave down for each of Z = CHO, COCH3, and CN and are consistent with a change from rate-determining nucleophilic attack for the more basic pyridines to rate-determining protonation of the carbanionic intermediate by a water molecule for less basic pyridines and the corresponding microscopic reverse processes in the elimination reactions. The "break" in these Bronsted-type plots is shown to occur at a pyridine basicity that is a function of the Z-activating substituent. Bronsted beta-1g, and beta(nuc) are evaluated for each rate-determining step (wherever accessible); these two parameters are shown to pass through minima as a function of reactivity. beta(eq), is shown to be a simple linear function of reactivity (as log k(Nu)) for nucleophilic addition to the acceptor species, although K(eq) is relatively insensitive to the nature of the Z-activating substituent.

  DOI：

  10.1021/jo00039a013
• 作为产物：
  描述：

  4-hydroxypyridine 、 丙烯醛 在 hydroxide 水 作用下， 生成 3-(4-Oxopyridin-1-yl)propanal
  参考文献：
  名称：

  Rate-determining steps in Michael-type additions and E1cb reactions in aqueous solution

  摘要：

  Rates of equilibration of a series of 10 substituted pyridines and five Michael acceptors (CH2=CHZ, Z = CHO, COCH3, SO2CH3, CN, and CONH2) with the corresponding N(ZCH2CH2) pyridinium cations have been measured in aqueous solution at ionic strength 0.1 and 25-degrees-C. Analysis of the dependence of the pseudo-first-order rate constants for equilibration as a function of acceptor concentration and of pH allows the evaluation of the second-order rate constants (k(Nu)) for the nucleophilic attack of each of these pyridines upon each of these acceptors and also the second-order rate constants (k(OH)) for the hydroxide ion catalyzed E1cb elimination reaction which is the microscopic reverse of each of these Michael-type addition reactions. Bronsted-type plots for each of these processes as a function of the basicity of the substituted pyridine are concave down for each of Z = CHO, COCH3, and CN and are consistent with a change from rate-determining nucleophilic attack for the more basic pyridines to rate-determining protonation of the carbanionic intermediate by a water molecule for less basic pyridines and the corresponding microscopic reverse processes in the elimination reactions. The "break" in these Bronsted-type plots is shown to occur at a pyridine basicity that is a function of the Z-activating substituent. Bronsted beta-1g, and beta(nuc) are evaluated for each rate-determining step (wherever accessible); these two parameters are shown to pass through minima as a function of reactivity. beta(eq), is shown to be a simple linear function of reactivity (as log k(Nu)) for nucleophilic addition to the acceptor species, although K(eq) is relatively insensitive to the nature of the Z-activating substituent.

  DOI：

  10.1021/jo00039a013

文献信息

• Rate-determining steps in Michael-type additions and E1cb reactions in aqueous solution
  作者：Christina K. M. Heo、John W. Bunting

  DOI：10.1021/jo00039a013

  日期：1992.6

  Rates of equilibration of a series of 10 substituted pyridines and five Michael acceptors (CH2=CHZ, Z = CHO, COCH3, SO2CH3, CN, and CONH2) with the corresponding N(ZCH2CH2) pyridinium cations have been measured in aqueous solution at ionic strength 0.1 and 25-degrees-C. Analysis of the dependence of the pseudo-first-order rate constants for equilibration as a function of acceptor concentration and of pH allows the evaluation of the second-order rate constants (k(Nu)) for the nucleophilic attack of each of these pyridines upon each of these acceptors and also the second-order rate constants (k(OH)) for the hydroxide ion catalyzed E1cb elimination reaction which is the microscopic reverse of each of these Michael-type addition reactions. Bronsted-type plots for each of these processes as a function of the basicity of the substituted pyridine are concave down for each of Z = CHO, COCH3, and CN and are consistent with a change from rate-determining nucleophilic attack for the more basic pyridines to rate-determining protonation of the carbanionic intermediate by a water molecule for less basic pyridines and the corresponding microscopic reverse processes in the elimination reactions. The "break" in these Bronsted-type plots is shown to occur at a pyridine basicity that is a function of the Z-activating substituent. Bronsted beta-1g, and beta(nuc) are evaluated for each rate-determining step (wherever accessible); these two parameters are shown to pass through minima as a function of reactivity. beta(eq), is shown to be a simple linear function of reactivity (as log k(Nu)) for nucleophilic addition to the acceptor species, although K(eq) is relatively insensitive to the nature of the Z-activating substituent.