3-(4-Aminopyridin-1-ium-1-yl)propanamide | 141375-73-7

• 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-Aminopyridin-1-ium-1-yl)propanamide
• CAS: 141375-73-7
• 化学式: C₈H₁₂N₃O
• 分子量: 166.203
• InChiKey: DBAFEKIUINIOSB-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 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：
  73
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-Aminopyridin-1-ium-1-yl)propanamide 在 hydroxide 水 作用下， 生成 4-氨基吡啶 、 丙烯酰胺
  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-氨基吡啶 、 丙烯酰胺 在 hydroxide 水 作用下， 生成 3-(4-Aminopyridin-1-ium-1-yl)propanamide
  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

• ONE-POT PROCESS FOR THE SYNTHESIS OF DALFAMPRIDINE
  申请人：GARAVAGLIA Fabio

  公开号：US20110319628A1

  公开（公告）日：2011-12-29

  A process for the preparation of Dalfampridine (1), 4-aminopyridine, starting from 4-pyridinecarbonitrile using a one-pot procedure. Said process is carried out with no need for isolating intermediates and is particularly advantageous as far as environment, yields, productivity and purity of the resulting product are concerned, both in the reaction mixture and in the isolated crystal.

  一种制备达法普林（1），也就是4-氨基吡啶的工艺流程，起点为4-吡啶腈，采用一锅法。该工艺流程无需分离中间体，特别优越之处在于环境、产率、生产率和所得产物的纯度，无论是在反应混合物中还是在分离的晶体中。
• US8877935B2
  申请人：——

  公开号：US8877935B2

  公开（公告）日：2014-11-04
• 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.