4′-hydroxy-3,3′,4-trichlorobiphenyl | 124882-64-0

• 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′-hydroxy-3,3′,4-trichlorobiphenyl
• 英文别名: 3,3',4'-trichloro-4-hydroxybiphenyl；4'-hydroxy-3,3',4-trichlorobiphenyl；4-hydroxy-3,3',4'-trichlorobiphenyl；3,3',4'-trichlorobiphenyl-4-ol；4'-HO-3,3',4-TCB；4'-OH PCB 35；2-Chloro-4-(3,4-dichlorophenyl)phenol
• CAS: 124882-64-0
• 化学式: C₁₂H₇Cl₃O
• 分子量: 273.546
• InChiKey: VQMNVNJOJQZHKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4′-hydroxy-3,3′,4-trichlorobiphenyl 在 lithium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 18.0h， 生成 6-<(3,3',4'-trichlorobiphenyl-4-yl)oxy>hexanoic acid
  参考文献：
  名称：

  Derivation and Properties of Recombinant Fab Antibodies to Coplanar Polychlorinated Biphenyls

  摘要：

  Recombinant Fab antibodies (rFabs) specific for coplanar polychlorinated biphenyls (PCBs) were derived from a hybridoma cell line (Chiu et al. Anal. Chem. 1995, 67, 3829-3839). Immunoglobulin V-H-C-H1 and V-L-C-L sequences from S2B1 messenger RNA were amplified by PCR and cloned into the M13 phagemid vector pComb3H. Phage displaying rFab were enriched by panning on a PCB hapten conjugate and expressed as soluble rFabs in Escherichia coli XL-1 Blue. Two rFab clones competitively bound PCBs 77 and 126 with half-maximal inhibition (I-50) of 10-13 ppb in indirect and direct enzyme immunoassays (EIAs), with selectivity nearly identical to that of whole S2B1 IgG and its Fab fragments prepared by papa-in digestion. These results, and comparison of N-terminal amino acid sequences of MAb S2B1 and the rFab, indicated that rFab S2B1 is a functional copy of the MAb. The rFab S2B1 sequences have 75-89% sequence identity with antibodies that bind nitrophenyl haptens and are being used to construct a three-dimensional computational model of the PCB binding site.

  DOI：

  10.1021/jf991208a
• 作为产物：
  描述：

  2,3,6-三氯苯酚 在 四(三苯基膦)钯 sodium hydroxide 、 氢溴酸 、 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 36.5h， 生成 4′-hydroxy-3,3′,4-trichlorobiphenyl
  参考文献：
  名称：

  Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling

  摘要：

  An improved synthesis of hydroxylated polychlorinated biphenyls (PCBs) which are structurally related to the major hydroxy PCB, congeners identified in human plasma is described. The coupling of (chlorinated) aryl boronic acids with bromochloro anisoles using the standard conditions of the Suzuki coupling gave the desired hydroxylated PCB metabolites in good to excellent yields. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0045-6535(01)00052-2

文献信息

• A Monoclonal Immunoassay for the Coplanar Polychlorinated Biphenyls
  作者：Ya-Wen. Chiu、Robert E. Carlson、Karen L. Marcus、Alexander E. Karu

  DOI：10.1021/ac00117a003

  日期：1995.11.1

  Polychlorinated biphenyls (PCBs) are ubiquitous environmental pollutants with diverse toxic, teratogenic, reproductive, immunotoxic, and tumorigenic effects, Three of the least abundant of the 209 PCB isomers (congeners) are the most toxic and most difficult to quantify, These are 3,4,3',4'-tetrachlorobiphenyl, 3,4,3',4',5'-pentachlorobiphetayl, and 3,4,5,3',4',5'-hexachlorobiphenyl (IUPAC No, 77, 126, and 169, respectively), An immunizing hapten was designed to retain the 3,4,3',4' chlorine-substitution pattern and coplanarity characteristic of these toxic congeners, The optimal competitors for immunoassay were weaker binding distinctive single-ring fragments of the PCBs, A monoclonal antibody designated S2B1 was derived and used in direct (antibody-capture) competitive enzyme immunoassays (EIAs). The EIAs are highly specific for non-ortho-substituted congeners and do not recognize the more prevalent but much less toxic noncoplanar PCB congeners or 2,3,7,8-tetrachlorodibenzo-p-dioxin, 2,3,7,8-tetrachlorodibenzofuran, or dichlorobenzenes, Hapten and competitor design for this assay suggests a basis for development of sensitive EIAs for other classes of PCB congeners.
• US6204005B1
  申请人：——

  公开号：US6204005B1

  公开（公告）日：2001-03-20
• Derivation and Properties of Recombinant Fab Antibodies to Coplanar Polychlorinated Biphenyls
  作者：Ya-Wen Chiu、Rongliang Chen、Qing X. Li、Alexander E. Karu

  DOI：10.1021/jf991208a

  日期：2000.6.1

  Recombinant Fab antibodies (rFabs) specific for coplanar polychlorinated biphenyls (PCBs) were derived from a hybridoma cell line (Chiu et al. Anal. Chem. 1995, 67, 3829-3839). Immunoglobulin V-H-C-H1 and V-L-C-L sequences from S2B1 messenger RNA were amplified by PCR and cloned into the M13 phagemid vector pComb3H. Phage displaying rFab were enriched by panning on a PCB hapten conjugate and expressed as soluble rFabs in Escherichia coli XL-1 Blue. Two rFab clones competitively bound PCBs 77 and 126 with half-maximal inhibition (I-50) of 10-13 ppb in indirect and direct enzyme immunoassays (EIAs), with selectivity nearly identical to that of whole S2B1 IgG and its Fab fragments prepared by papa-in digestion. These results, and comparison of N-terminal amino acid sequences of MAb S2B1 and the rFab, indicated that rFab S2B1 is a functional copy of the MAb. The rFab S2B1 sequences have 75-89% sequence identity with antibodies that bind nitrophenyl haptens and are being used to construct a three-dimensional computational model of the PCB binding site.
• Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling
  作者：Hans-Joachim Lehmler、Larry W. Robertson

  DOI：10.1016/s0045-6535(01)00052-2

  日期：2001.12

  An improved synthesis of hydroxylated polychlorinated biphenyls (PCBs) which are structurally related to the major hydroxy PCB, congeners identified in human plasma is described. The coupling of (chlorinated) aryl boronic acids with bromochloro anisoles using the standard conditions of the Suzuki coupling gave the desired hydroxylated PCB metabolites in good to excellent yields. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials. (C) 2001 Elsevier Science Ltd. All rights reserved.