3,5-dichloro-6-[(2,4-dichloro-3-methyl-5,6-dioxocyclohexa-1,3-dien-1-yl)methyl]-4-methylcyclohexa-3,5-diene-1,2-dione | 153444-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dichloro-6-[(2,4-dichloro-3-methyl-5,6-dioxocyclohexa-1,3-dien-1-yl)methyl]-4-methylcyclohexa-3,5-diene-1,2-dione
• CAS: 153444-05-4
• 化学式: C₁₅H₈Cl₄O₄
• 分子量: 394.038
• InChiKey: CEUNQABTBBISGX-UHFFFAOYSA-N

物化性质

• 沸点：
  423.3±45.0 °C(predicted)
• 密度：
  1.61±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-6-[(2,4-dichloro-3-methyl-5,6-dioxocyclohexa-1,3-dien-1-yl)methyl]-4-methylcyclohexa-3,5-diene-1,2-dione 在 sodium tetrahydroborate 、 水 、 氯 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3,5-Dichloro-6-(2,4-dichloro-5,6-dihydroxy-3-methyl-benzyl)-4-methyl-[1,2]benzoquinone
  参考文献：
  名称：

  木质素模型二聚体依次与氯和氢氧化钠反应。

  摘要：

  Dimer 9, which-is;representative of diaryl methane structures reported present in residual lignin, was reacted with aqueous chlorine at 50 degrees C. The major product was identified as the tetrachloroquinone dimer 13 (x = 2, y 2).; Similar reaction of the tetrachlorocatechol dimer 12 with aqueous chlorine gave a mixture of the tetlachloroquinones 15 and 16. When the mixture of the quinones was reacted with 2.5% sodium hydroxide, an intramolecular oxidation-reduction (Cannizzaro) reaction with the simultaneous loss of two chlorine atoms occurred as the main reaction. The products, 21, were characterized as having a chlorine-free muconic acid lactone group attached to a dichlorocatechol. A third product 17 from the reaction with sodium hydroxide appeared to result from simple displacement of the two chlorine atoms in the quinone ring of 15 by hydroxyl groups. The results provide some clarification of the reactions occurring during classical chlorine bleaching. The results are also in agreement with literature reports concerning some of the-structural characteristics of the high mass material.

  DOI：

  10.1021/es00053a007
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯酚 在 sodium hydroxide 、 水 、 氯 作用下， 反应 2.75h， 生成 3,5-dichloro-6-[(2,4-dichloro-3-methyl-5,6-dioxocyclohexa-1,3-dien-1-yl)methyl]-4-methylcyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  木质素模型二聚体依次与氯和氢氧化钠反应。

  摘要：

  Dimer 9, which-is;representative of diaryl methane structures reported present in residual lignin, was reacted with aqueous chlorine at 50 degrees C. The major product was identified as the tetrachloroquinone dimer 13 (x = 2, y 2).; Similar reaction of the tetrachlorocatechol dimer 12 with aqueous chlorine gave a mixture of the tetlachloroquinones 15 and 16. When the mixture of the quinones was reacted with 2.5% sodium hydroxide, an intramolecular oxidation-reduction (Cannizzaro) reaction with the simultaneous loss of two chlorine atoms occurred as the main reaction. The products, 21, were characterized as having a chlorine-free muconic acid lactone group attached to a dichlorocatechol. A third product 17 from the reaction with sodium hydroxide appeared to result from simple displacement of the two chlorine atoms in the quinone ring of 15 by hydroxyl groups. The results provide some clarification of the reactions occurring during classical chlorine bleaching. The results are also in agreement with literature reports concerning some of the-structural characteristics of the high mass material.

  DOI：

  10.1021/es00053a007

文献信息

• McKague Bruce, Reeve Douglas W., Environ. Sci. and Technol, 28 (1994) N 4, S 573-576
  作者：McKague Bruce, Reeve Douglas W.

  DOI：——

  日期：——