4,5,6,2',5'-pentachloro-3-methanesulfonylbiphenyl | 104086-09-1

• 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: 4,5,6,2',5'-pentachloro-3-methanesulfonylbiphenyl
• 英文别名: 2,2',3,4,5'-Pentachloro-5-(methylsulfonyl)-1,1'-biphenyl；2,3,4-trichloro-1-(2,5-dichlorophenyl)-5-methylsulfonylbenzene
• CAS: 104086-09-1
• 化学式: C₁₃H₇Cl₅O₂S
• 分子量: 404.528
• InChiKey: IIAWWLXDSCCHGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 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：

  (2,5-Dichloro-phenyl)-trimethyl-stannane 、 2,3,4-Trichloro-1-iodo-5-methanesulfonyl-benzene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以72%的产率得到4,5,6,2',5'-pentachloro-3-methanesulfonylbiphenyl
  参考文献：
  名称：

  An alternative synthesis of chlorinated biphenyl methylsulfonyl metabolites

  摘要：

  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.

  DOI：

  10.1016/0045-6535(95)00331-2

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.