2,3,5-trichloro-6-(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione | 144106-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-trichloro-6-(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,3,5-Trichloro-6-piperidin-1-ylcyclohexa-2,5-diene-1,4-dione
• CAS: 144106-39-8
• 化学式: C₁₁H₁₀Cl₃NO₂
• 分子量: 294.565
• InChiKey: NOXYFACSVRILKL-UHFFFAOYSA-N

物化性质

• 沸点：
  354.2±42.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  哌啶 、 四氯苯醌 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 0.12h， 生成 2,3,5-trichloro-6-(piperidin-1-yl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Spectrophotometric determination of amines with p-chloranil

  摘要：

  DOI：

  10.1021/ac00277a019

文献信息

• Quantification of the Ambident Electrophilicities of Halogen-Substituted Quinones
  作者：Xingwei Guo、Herbert Mayr

  DOI：10.1021/ja505613b

  日期：2014.8.13

  Kinetics and mechanisms of the reactions of p-quinone, 2,5-dichloro-p-quinone, 2,3,4,5-tetrachloro-p-quinone (chloranil), 2,3,4,5-tetrafluoro-p-quinone (fluoranil), and 3,4,5,6-tetrachloro-o-quinone with pi-nudeophiles (siloxyalkenes, enamines) and amines have been investigated. Products arising from nudeophilic attack at all conceivable sites, that is, at C and O of the carbonyl groups (pathways a, b) as well as at halogenated and nonhalogenated conjugate positions (pathways c, d), were observed. The partial rate constants for the C-attack pathways (a, c, d), which are derived from the photometrically determined second-order rate constants and the product ratios followed the linear free energy relationship log k (20 degrees C) = s(N)(E + (Mayr, H.; et al. J. Am. Chem. Soc. 2001, 123, 9500-9512). It was, therefore, possible to calculate the electrophilicity parameters E of the different positions of the quinones from log k (20 degrees C) and the N and s(N) parameters of the nucleophilic reaction partners, which have previously been derived from their reactions with benzhydrylium ions. Almost all rate constants for the C-attack pathways (a, c, d) were considerably larger than those calculated for the corresponding SET processes, indicating the operation of polar mechanisms. SET mechanisms may only account for the formation of the products formed via O-attack. With the E parameters determined in this work, it is now possible to predict rate constants for the reactions of these quinones with a large variety of nudeophiles and, thus, envisage unprecedented reactions of quinones.