2-amino-3,7,8-trichlorodibenzo-p-dioxin | 71721-80-7

• 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: 2-amino-3,7,8-trichlorodibenzo-p-dioxin
• 英文别名: 2-amino-3,7,8-trichlorodibenzodioxin；Dibenzo(b,e)(1,4)dioxin-2-amine, 3,7,8-trichloro-；3,7,8-trichlorodibenzo-p-dioxin-2-amine
• CAS: 71721-80-7
• 化学式: C₁₂H₆Cl₃NO₂
• 分子量: 302.544
• InChiKey: UGDXYGVQWQOTDX-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±45.0 °C(Predicted)
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3,7,8-trichlorodibenzo-p-dioxin 、 2-methacryloyloxybenzoyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(2-(3,7,8-trichlorodibenzodioxinyl))-2-methacryloyloxybenzamide
  参考文献：
  名称：

  A Novel Approach to the Molecular Imprinting of Polychlorinated Aromatic Compounds

  摘要：

  The aim of this investigation was to determine whether relatively weak interactions, such as hydrogen bonds to aromatic chlorine atoms and interactions involving aromatic pi electrons could be exploited within artificial receptors, constructed using the technique of molecular imprinting. For the purposes of this investigation we chose 2,3,7,8-tetrachlorodibenzodioxin (TCDD)as the model target. Imprinted polymers have been prepared with two new templates designed to create recognition sites for TCDD. The first of these, the bis-N-(4-vinylphenyl)urea derivative of 2,8-dichloro-3,7-diaminodibenzodioxin, employed a carbonyl spacer to introduce aromatic amines into the polymer after reductive cleavage of the template. The second, N-(2-(3,7,8-trichlorodibenzodioxinyl))-2-methacryloyloxybenzamide, incorporated a salicylic acid spacer and introduced a methacrylic acid residue into the polymer following hydrolysis. Both amine and acid groups were positioned in such a way as to interact with TCDD through the formation of weak hydrogen bonds to aromatic chlorine atoms. A second recognition element was introduced into the binding sites by the inclusion of a polymerizable, electron-rich, aromatic ether capable of forming pi-pi interactions with the electron-deficient dioxin molecule. Polymers imprinted with either template showed significantly higher uptake of TCDD than the corresponding nonimprinted controls, even at concentrations as low as 2 nM.

  DOI：

  10.1021/ja9818295
• 作为产物：
  描述：

  4-氯邻苯二酚 在 镍 六甲基磷酰三胺 、 氢氧化钾 、 硝酸铵 、 potassium carbonate 、 一水合肼 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 硝基甲烷 、 乙醇 为溶剂， 生成 2-amino-3,7,8-trichlorodibenzo-p-dioxin
  参考文献：
  名称：

  A Novel Approach to the Molecular Imprinting of Polychlorinated Aromatic Compounds

  摘要：

  The aim of this investigation was to determine whether relatively weak interactions, such as hydrogen bonds to aromatic chlorine atoms and interactions involving aromatic pi electrons could be exploited within artificial receptors, constructed using the technique of molecular imprinting. For the purposes of this investigation we chose 2,3,7,8-tetrachlorodibenzodioxin (TCDD)as the model target. Imprinted polymers have been prepared with two new templates designed to create recognition sites for TCDD. The first of these, the bis-N-(4-vinylphenyl)urea derivative of 2,8-dichloro-3,7-diaminodibenzodioxin, employed a carbonyl spacer to introduce aromatic amines into the polymer after reductive cleavage of the template. The second, N-(2-(3,7,8-trichlorodibenzodioxinyl))-2-methacryloyloxybenzamide, incorporated a salicylic acid spacer and introduced a methacrylic acid residue into the polymer following hydrolysis. Both amine and acid groups were positioned in such a way as to interact with TCDD through the formation of weak hydrogen bonds to aromatic chlorine atoms. A second recognition element was introduced into the binding sites by the inclusion of a polymerizable, electron-rich, aromatic ether capable of forming pi-pi interactions with the electron-deficient dioxin molecule. Polymers imprinted with either template showed significantly higher uptake of TCDD than the corresponding nonimprinted controls, even at concentrations as low as 2 nM.

  DOI：

  10.1021/ja9818295

文献信息

• Monoclonal antibodies reactive with chlorinated dibenzo-p-dioxins and method of preparing and using same
  申请人：WESTINGHOUSE ELECTRIC CORPORATION

  公开号：EP0258006A2

  公开（公告）日：1988-03-02

  Monoclonal antibodies that react with chlorinated dibenzo-p-dioxins, particularly, 2,3,7,8-tetrachlorodi­benzo-p-dioxin. Also a method of producing such antibodies by producing an immunogenic conjugate of a chlorinated dibenzo-p-dioxin and a macromolecule carrier, immunizing an animal with the conjugate, obtaining antibody-producing cells from the animal, fusing the cells with tumor cells to produce hybridomas, selecting from among the hybridomas at least one that produces antibodies reactive with the chlorinated dioxin, and recovering the antibodies. Also analytic, diagnostic, investigational, separatory and other methods of using the antibodies, and compositions con­taining the antibodies for such uses.

  与氯化二苯并-对-二恶英，特别是 2，3，7，8-四氯二苯并-对-二恶英反应的单克隆抗体。 还有一种生产这种抗体的方法，即生产氯化二苯并-对-二恶英和大分子载体的免疫原性共轭物，用共轭物免疫动物，从动物身上获得产生抗体的细胞，将细胞与肿瘤细胞融合产生杂交瘤，从杂交瘤中至少选择一种产生与氯化二恶英反应的抗体，并回收抗体。 还有使用抗体的分析、诊断、研究、分离和其他方法，以及含有这种抗体的组合物。
• Kuntsevich, A. D.; Golovkov, V. F.; Chernov, S. A., Russian Journal of General Chemistry, 1993, vol. 63, # 8.2., p. 1279 - 1286
  作者：Kuntsevich, A. D.、Golovkov, V. F.、Chernov, S. A.

  DOI：——

  日期：——
• Kuntsevich, A. D.; Golovkov, V. F.; Rembovskii, V. R., Doklady Chemistry, 1993, vol. 330, # 1-3, p. 133 - 136
  作者：Kuntsevich, A. D.、Golovkov, V. F.、Rembovskii, V. R.、Chernov, S. A.

  DOI：——

  日期：——
• US5128244A
  申请人：——

  公开号：US5128244A

  公开（公告）日：1992-07-07
• A Novel Approach to the Molecular Imprinting of Polychlorinated Aromatic Compounds
  作者：Markus Lübke、Michael J. Whitcombe、Evgeny N. Vulfson

  DOI：10.1021/ja9818295

  日期：1998.12.1

  The aim of this investigation was to determine whether relatively weak interactions, such as hydrogen bonds to aromatic chlorine atoms and interactions involving aromatic pi electrons could be exploited within artificial receptors, constructed using the technique of molecular imprinting. For the purposes of this investigation we chose 2,3,7,8-tetrachlorodibenzodioxin (TCDD)as the model target. Imprinted polymers have been prepared with two new templates designed to create recognition sites for TCDD. The first of these, the bis-N-(4-vinylphenyl)urea derivative of 2,8-dichloro-3,7-diaminodibenzodioxin, employed a carbonyl spacer to introduce aromatic amines into the polymer after reductive cleavage of the template. The second, N-(2-(3,7,8-trichlorodibenzodioxinyl))-2-methacryloyloxybenzamide, incorporated a salicylic acid spacer and introduced a methacrylic acid residue into the polymer following hydrolysis. Both amine and acid groups were positioned in such a way as to interact with TCDD through the formation of weak hydrogen bonds to aromatic chlorine atoms. A second recognition element was introduced into the binding sites by the inclusion of a polymerizable, electron-rich, aromatic ether capable of forming pi-pi interactions with the electron-deficient dioxin molecule. Polymers imprinted with either template showed significantly higher uptake of TCDD than the corresponding nonimprinted controls, even at concentrations as low as 2 nM.