1,2-二氯-5-(3,4-二氯苯基)-3-甲基磺酰基苯 | 104104-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-二氯-5-(3,4-二氯苯基)-3-甲基磺酰基苯
• 中文别名: 3-甲磺酰-4,5,3',4'-四氯联苯基
• 英文名称: 3-methylsulfone-3',4,4',5-tetrachlorobiphenyl
• 英文别名: 5-Methylsulphonyl-3,3',4,4'-tetrachlorobiphenyl；4,5,3',4'-tetrachloro-3-methanesulfonylbiphenyl；3-Methylsulfonyl-4,5,3',4'-tetrachlorobiphenyl；1,2-dichloro-5-(3,4-dichlorophenyl)-3-methylsulfonylbenzene
• CAS: 104104-34-9
• 化学式: C₁₃H₈Cl₄O₂S
• 分子量: 370.083
• InChiKey: NPOQAWWYZIAGCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-Dichlorothioanisole 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 生成 1,2-二氯-5-(3,4-二氯苯基)-3-甲基磺酰基苯
  参考文献：
  名称：

  Metabolism of 3,3′,4,4′-tetrachlorobiphenyl via sulphur-containing pathway in rat: liver-specific retention of methylsulphonyl metabolite

  摘要：

  1. Single doses of 3,3',4,4'-tetrachlorobiphenyl (TCB) were administered intraperitoneally to the male Wistar rat for metabolism studies.2. Seven sulphur-containing metabolites of TCB were isolated from faeces, in addition to previously reported 4-hydroxy-3,3',4',5-tetrachlorobiphenyl and 5-hydroxy-TCB. Major sulphur-containing metabolites were 5- and 6-methylthio-TCBs, and 6-methylsulphonyl-3-methylthio-3',4,4'-trichlorobiphenyl.3. The faecal excretions of hydroxy metabolites, methylthio metabolites and unchanged TCB accounted for 7.1, 0.5 and 0.3% of the dose respectively within 4 days after administration.4. 5-Methylsulphonyl-TCB was detected and selectively retained in liver. The concentration ratio of 5-methylsulphonyl-TCB and unchanged TCB in liver was 1:4.5. Following administration of 5- and 6-methylsulphonyl-TCBs to rat, 5-methylsulphonyl-TCB was localized in liver, whereas 6-methylsulphonyl-TCB was rapidly biotransformed to 6-methylsulphonyl-3-methylthio-3',4,4'-trichlorobiphenyl and excreted in the faeces.

  DOI：

  10.1080/004982597240190

文献信息

• An alternative synthesis of chlorinated biphenyl methylsulfonyl metabolites
  作者：Richard D. Mortimer、W.Harvey Newsome

  DOI：10.1016/0045-6535(95)00331-2

  日期：1996.3

  Published methods of synthesizing chlorinated biphenyl methylsulfones require the separation of a complex mixture of impurities and isomers using both normal and reverse phase HPLC. Even with semi-preparative scale equipment, the process is tedious and time-consuming. In this report, the palladium-catalyzed addition of an aryl iodide to an aryl trimethylstannane has been exploited to produce these compounds in high purity (greater than or equal to 99%) using conventional techniques of purification. The reaction has been demonstrated for a group of methylsulfonyl CBs representing 0 to 3 ortho-chlorine interactions between the biphenyl rings and with the methylsulfonyl group at either the 3- or 4-position.
• Metabolism of 3,3′,4,4′-tetrachlorobiphenyl via sulphur-containing pathway in rat: liver-specific retention of methylsulphonyl metabolite
  作者：K. HARAGUCHI*、Y. KATO、Y. MASUDA、R. KIMURA

  DOI：10.1080/004982597240190

  日期：1997.1

  1. Single doses of 3,3',4,4'-tetrachlorobiphenyl (TCB) were administered intraperitoneally to the male Wistar rat for metabolism studies.2. Seven sulphur-containing metabolites of TCB were isolated from faeces, in addition to previously reported 4-hydroxy-3,3',4',5-tetrachlorobiphenyl and 5-hydroxy-TCB. Major sulphur-containing metabolites were 5- and 6-methylthio-TCBs, and 6-methylsulphonyl-3-methylthio-3',4,4'-trichlorobiphenyl.3. The faecal excretions of hydroxy metabolites, methylthio metabolites and unchanged TCB accounted for 7.1, 0.5 and 0.3% of the dose respectively within 4 days after administration.4. 5-Methylsulphonyl-TCB was detected and selectively retained in liver. The concentration ratio of 5-methylsulphonyl-TCB and unchanged TCB in liver was 1:4.5. Following administration of 5- and 6-methylsulphonyl-TCBs to rat, 5-methylsulphonyl-TCB was localized in liver, whereas 6-methylsulphonyl-TCB was rapidly biotransformed to 6-methylsulphonyl-3-methylthio-3',4,4'-trichlorobiphenyl and excreted in the faeces.