(E)-3-(2,3,7,8-Tetrachloro-dibenzo[1,4]dioxin-1-yl)-acrylic acid ethyl ester | 207724-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 英文名称: (E)-3-(2,3,7,8-Tetrachloro-dibenzo[1,4]dioxin-1-yl)-acrylic acid ethyl ester
• CAS: 207724-30-9
• 化学式: C₁₇H₁₀Cl₄O₄
• 分子量: 420.076
• InChiKey: GQYBTFXTDITZTG-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,3,7,8-Tetrachloro-dibenzo[1,4]dioxin-1-yl)-acrylic acid ethyl ester 在 氢氧化钾 作用下， 以 乙二醇甲醚 为溶剂， 以27%的产率得到trans-3-(2,3,7,8-Tetrachlorodibenzo-p-dioxin-1-yl) propenoic acid
  参考文献：
  名称：

  Hapten Synthesis and Antibody Development for Polychlorinated Dibenzo-p-dioxin Immunoassays

  摘要：

  This paper reports the synthesis of haptens and the generation and preliminary evaluation of polyclonal antibodies for the detection of dioxins such as TCDD (2,3,7,8-tetrachlorodibenzo-p-dioxin) by ELISA (enzyme-linked immunosorbent assay). These novel haptens contain unsaturation between the halogenated dibenzo-p-dioxin ring system and the protein to which it is conjugated, presenting a rigid handle structure. The substitution pattern is identical with or similar to that of TCDD (i.e., 2,3,7,8- or 1,2,3,7,8-). Finally, the haptens lack polar groups for hydrogen bonding. In direct binding assays using the new polyclonal antibodies there was excellent recognition of hapten-protein conjugates, including recognition of those hapten conjugates that were not used as immunogens (i.e., assay systems heterologous in hapten structure). These haptens do elicit selective immune responses in rabbits. Their evaluation in an ELISA format demonstrated the usefulness of these haptens for the detection of dioxins. An IC50 of 0.8 ng/well (16 ng/mL) was observed for an unoptimized system that used 2,3,7-trichloro-8-methyldibenzo-p-dioxin as an analytical surrogate standard.

  DOI：

  10.1021/jf970716m
• 作为产物：
  描述：

  2,3,6-三氯苯甲醛 在 二苯并-18-冠醚-6 、 硫酸 、 potassium tert-butylate 、 potassium carbonate 、 potassium nitrate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 生成 (E)-3-(2,3,7,8-Tetrachloro-dibenzo[1,4]dioxin-1-yl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Hapten Synthesis and Antibody Development for Polychlorinated Dibenzo-p-dioxin Immunoassays

  摘要：

  This paper reports the synthesis of haptens and the generation and preliminary evaluation of polyclonal antibodies for the detection of dioxins such as TCDD (2,3,7,8-tetrachlorodibenzo-p-dioxin) by ELISA (enzyme-linked immunosorbent assay). These novel haptens contain unsaturation between the halogenated dibenzo-p-dioxin ring system and the protein to which it is conjugated, presenting a rigid handle structure. The substitution pattern is identical with or similar to that of TCDD (i.e., 2,3,7,8- or 1,2,3,7,8-). Finally, the haptens lack polar groups for hydrogen bonding. In direct binding assays using the new polyclonal antibodies there was excellent recognition of hapten-protein conjugates, including recognition of those hapten conjugates that were not used as immunogens (i.e., assay systems heterologous in hapten structure). These haptens do elicit selective immune responses in rabbits. Their evaluation in an ELISA format demonstrated the usefulness of these haptens for the detection of dioxins. An IC50 of 0.8 ng/well (16 ng/mL) was observed for an unoptimized system that used 2,3,7-trichloro-8-methyldibenzo-p-dioxin as an analytical surrogate standard.

  DOI：

  10.1021/jf970716m