N-phenylsulfonyl-5,6-dichloro-2-methyl-4-aminophenol | 314751-53-6

• 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: N-phenylsulfonyl-5,6-dichloro-2-methyl-4-aminophenol
• 英文别名: Benzenesulfonamide, N-(2,3-dichloro-4-hydroxy-5-methylphenyl)-；N-(2,3-dichloro-4-hydroxy-5-methylphenyl)benzenesulfonamide
• CAS: 314751-53-6
• 化学式: C₁₃H₁₁Cl₂NO₃S
• 分子量: 332.207
• InChiKey: IMWWNIPSXVIARR-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  466.8±55.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-phenylsulfonyl-5,6-dichloro-2-methyl-4-aminophenol 在 氯 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 4-phenylsulfonylimino-2,3,5,6-tetrachloro-6-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: IV. Chlorination and bromination of N-arylsulfonyl-2(3)-methyl(2-chloro)-1,4-benzoquinone monoimines

  摘要：

  The addition of halogens to N-arylsulfonyl-1,4-benzoquinone imines, which exist in a solution as Z and E isomers, is controlled by the steric factor. Z-E Isomerization strongly affects the stability of cyclohexene structures formed by halogenation of 1,4-benzoquinone imines. The halogenation of N-arylsulfonyl-1,4-benzoquinone imines was found to be accompanied by prototropic rearrangement.

  DOI：

  10.1134/s1070428006030031
• 作为产物：
  描述：

  N-phenylsulfonyl-2-methyl-1,4-benzoquinone imine 在 氯 作用下， 以 溶剂黄146 为溶剂， 以50%的产率得到N-phenylsulfonyl-5,6-dichloro-2-methyl-4-aminophenol
  参考文献：
  名称：

  摘要：

  The study of chlorination of N-(N-arylsulfonylarylimidoyl)-1,4-benzoquinone imines and of N-(N-arylsulfonylarylimidoyl)-1,4-aminophenols revealed that the dominant stage in the process was the formation of cyclohexene structures, 4-(N-arylsulfonylarylimidoyl)imino-2,5,6-trichloro-2-cyclohexene-1-ones, resulting from addition of a Cl-2 molecule across the C=C bond of the quinoid ring. These substances suffer a prototropic rearrangements yielding N-(N-arylsulfonylarylimidoyl)-2,3,6-trichloro-4-aminophenols. The latter are the most common reaction products. The products of deeper chlorination were also obtained.

  DOI：

  10.1023/a:1016555324390

文献信息

• Quantum-Chemical Study of the Structure of N-Substituted p-Quinonimines and Their Reactions with Hydrogen Halides
  作者：A. P. Avdeenko、S. A. Konovalova、K. S. Burmistrov、N. V. Toropin、A. V. Vakulenko

  DOI：10.1023/b:rujo.0000045185.66716.6c

  日期：2004.7

  Quantum-chemical calculations and X-ray diffraction data for a series of N-substituted p-quinonimines showed that the PM3 method is the most suitable for determination of geometric parameters of these compounds. Moreover, it can be used to predict the site of addition of chlorine and bromine in the hydrohalogenation reaction.