1-<4-Chlor-phenylamino>-buten-(1)-on-(3) | 51218-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<4-Chlor-phenylamino>-buten-(1)-on-(3)
• 英文别名: 4-(4-chloroanilino)but-3-en-2-one
• CAS: 51218-06-5
• 化学式: C₁₀H₁₀ClNO
• 分子量: 195.648
• InChiKey: LODXJZFOQAAXHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4,4-二甲氧基-2-丁酮 、 对氯苯胺 在 盐酸 作用下， 生成 1-<4-Chlor-phenylamino>-buten-(1)-on-(3)
  参考文献：
  名称：

  Über Derivate des Methyl-(β-phenylamino-vinyl)-ketons

  摘要：

  DOI：

  10.1002/ardp.19642970602

文献信息

• A kinetic study of alkaline hydrolysis of 1-arylimino-3-arylimino-1-butene.
  作者：Machiko ONO、Reiko TODORIKI、Shinzo TAMURA

  DOI：10.1248/cpb.37.2909

  日期：——

  Alkaline hydrolysis of 1-arylamino-3-arylimino-1-butene (1) was studied kinetically. The reaction proceeded in two ways; by hydrolysis at the 1-position of 1 to give β-arylaminocrotonaldehyde (2) and arylamine (pathway A), and by hydrolysis at the 3-position of 1 to give 4-arylamino-3-buten-2-one (3) and arylamine (pathway B), of which the former predominated. In the first step of pathway A, 1-position of 1 is attacked by hydroxide ion to give a tetrahedral intermediate which is then transformed into 2 and arylamine in the second step. Plots of the rate constants of pathway A, kA, vs. [OH-] were concave downward because the rates of the two steps are of similar order of magnitude. We were able to calculate the hydroxide ion-catalyzed rate constant (kOH1) of the first step of pathway A for 4 substrates, 1a-d. The kOH, 1s decreased with increasing electron-withdrawing effect of the aryl substituents. The reaction mechanism is discussed.

  对 1-芳基氨基-3-芳基亚氨基-1-丁烯（1）的碱性水解进行了动力学研究。反应以两种方式进行：在 1 的 1 位水解，生成 β-芳基氨基巴豆醛（2）和芳基胺（途径 A）；在 1 的 3 位水解，生成 4-芳基氨基-3-丁烯-2-酮（3）和芳基胺（途径 B），其中前者占主导地位。在途径 A 的第一步中，1 的 1 位受到氢氧根离子的攻击，生成四面体中间体，然后在第二步中转化为 2 和芳基胺。途径 A 的速率常数 kA 与[OH-]的关系图是向下凹的，因为两个步骤的速率数量级相似。我们能够计算出 4 种底物（1a-d）的途径 A 第一步在氢氧根离子催化下的速率常数（kOH1）。随着芳基取代基吸电子效应的增加，kOH, 1s 也随之降低。本文对反应机理进行了讨论。
• Remarkable catalytic effect of H+ in Michael-type additions of anilines to 3-butyn-2-one
  作者：Ik-Hwan Um、Eun-Ju Lee、Ji-Sook Min

  DOI：10.1016/s0040-4020(01)00981-4

  日期：2001.11

  Second-order rate constants (k(N)) for the Michael-type reaction of 3-butyn-2-one (1) with a series of anilines in H2O have been determined spectrophotometrically. The k(N) values are dependent on the free aniline fraction (F-N). The plot of log k(N) vs pK(a) of the conjugate acid of the anilines is linear for the reactions run at F-N=1.00. However, the Bronsted-type plot for the reactions performed at F-N=0.50 is nonlinear, suggesting a change in the reaction mechanism as the basicity of anilines changes. The analysis of the kinetic results has revealed that the reaction of anilines proceeds through the protonated form of the substrate 1 as well as the unprotonated. The protonated form of 1 is of the order of 10(9) times more reactive than the unprotonated form toward anilines. The contribution of the reaction with the protonated species to the k(N) is suggested to be responsible for the nonlinear Bronsted-type plot obtained for the reactions run at F-N=0.50. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Über Derivate des Methyl-(β-phenylamino-vinyl)-ketons
  作者：H. Böhme、G. Berg、H. Schneider

  DOI：10.1002/ardp.19642970602

  日期：——