1,2,3,4,6,7-六氯二苯并呋喃 | 79060-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 1,2,3,4,6,7-六氯二苯并呋喃
• 英文名称: 1,2,3,4,6,7-hexachlorodibenzofuran
• CAS: 79060-60-9
• 化学式: C₁₂H₂Cl₆O
• 分子量: 374.865
• InChiKey: SNWFMKXFMVHBKD-UHFFFAOYSA-N

物化性质

• 沸点：
  475.5±40.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)
• 保留指数：
  2707;2706;2706

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  19
• 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：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在现有文献中没有找到关于二苯并呋喃在哺乳动物体内的代谢信息。细菌Sphingomonas、Brevibacterium、Terrabacter和Staphylococcus auricularis通过二苯并呋喃4,4a-二加氧酶将二苯并呋喃降解为2,2',3-三羟基联苯。

No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

卤素代二苯并呋喃（PCDFs和PBDFs）与芳基烃受体（AhR）结合，增加了其在XRE（外源化合物响应元件）启动子区域激活转录的能力。具体来说，AhR与PCDF结合，将其转运到细胞核，并与芳烃核转运蛋白（ARNT）和外来化合物响应元件（XRE）一起增加CYP1A1和芳基烃羟化酶（CYP1B1）的表达。AhR信号还通过环氧合酶-2增加花生四烯酸转化为前列腺素，改变Wnt/β-连环蛋白信号，下调Sox9，并改变炎症细胞因子受体的信号传导。AhR信号还改变类固醇激素受体的蛋白体降解，改变细胞的UVB应激反应，并改变某些T细胞亚群的分化。由此产生的AhR介导的激活和改变导致体重减轻、癌症和胸腺萎缩（免疫和内分泌紊乱的特征），这是对PCDFs和相关有毒卤素代芳基烃的常见毒性反应。

Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 其对人类致癌性无法分类。

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

CDFs会导致呕吐和腹泻、贫血、更频繁的肺部感染、麻木以及对神经系统等其他影响，以及肝脏的轻微变化。然而，在摄入CDFs的人中没有发现永久性的肝脏变化或明确的肝脏损伤。

CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入 (L952) ; 皮肤 (L952) ; 口服 (L952)

Inhalation (L952) ; dermal (L952) ; oral (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

皮肤和眼部刺激，尤其是严重的痤疮、肤色变黑和带有分泌物的肿胀眼睑是CDF中毒最明显的健康影响。

Skin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为产物：
  描述：

  邻四氯苯醌 、 邻二氯苯 在 三氟甲磺酸 作用下， 生成 六氯二苯并呋喃 、 1,2,3,4,6,7-六氯二苯并呋喃
  参考文献：
  名称：

  超强酸促进多氯二苯并呋喃的合成

  摘要：

  多氯二苯并呋喃是一步制备的，其方法是邻氯苯腈与芳烃在三氟甲磺酸中缩合。提出了一种机制，该机制涉及单质子化醌（碳鎓离子）的形成，对芳烃的亲电攻击以及碳正离子中间体的环化。通过光谱学和理论研究进一步检查了化学反应。

  DOI：

  10.1016/j.tetlet.2016.06.100

文献信息

• [EN] SUBSTITUTED ARYL CYCLOALKANOL DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DERIVES DE CYCLOALCANOYL ARYLE SUBSTITUES ET PROCEDES D'UTILISATION DE CEUX-CI
  申请人：WYETH CORP

  公开号：WO2005037809A1

  公开（公告）日：2005-04-28

  The present invention is directed to substituted aryl cycloalkanoyl derivatives, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

  本发明涉及取代芳基环烷酰衍生物，含有这些衍生物的组合物，以及它们用于预防和治疗由单胺再摄取改善的病况的方法，包括但不限于血管运动症状（VMS）、性功能障碍、胃肠道和泌尿系统疾病、慢性疲劳综合征、纤维肌痛综合征、神经系统疾病，以及这些疾病的组合，尤其是从包括重性抑郁障碍、血管运动症状、压力和急迫性尿失禁、纤维肌痛、疼痛、糖尿病神经病变等病况中选出的那些病况。
• Process for Preparing Substituted Aryl Cycloalkanol Derivatives
  申请人：Gontcharov V. Alexander

  公开号：US20070129377A1

  公开（公告）日：2007-06-07

  Processes are disclosed for preparing substituted aryl cycloalkanol derivatives, particularly chiral substituted aryl cycloalkanol derivatives of the general formula:

  披露了制备取代芳基环烷醇衍生物的过程，特别是一般式如下的手性取代芳基环烷醇衍生物的过程：
• Substituted aryl cycloalkanol derivatives and methods of their use
  申请人：Trybulski John Eugene

  公开号：US20050143579A1

  公开（公告）日：2005-06-30

  The present invention is directed to substituted aryl cycloalkanoyl derivatives, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

  本发明涉及取代芳基环烷酰衍生物，含有这些衍生物的组合物，以及它们的使用方法，用于预防和治疗由单胺再摄取改善的病况，包括但不限于血管运动症状（VMS），性功能障碍，胃肠和泌尿系统疾病，慢性疲劳综合症，纤维肌痛综合症，神经系统疾病和其组合，特别是从包括重度抑郁症、血管运动症状、压力和切望性尿失禁、纤维肌痛、疼痛、糖尿病神经病变和其组合的一组疾病中选择的那些病状。
• SUBSTITUTED ARYL CYCLOALKANOL DERIVATIVES AND METHODS OF THEIR USE
  申请人：Trybulski Eugene John

  公开号：US20080153826A1

  公开（公告）日：2008-06-26

  The present invention is directed to substituted aryl cycloalkanoyl derivatives, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromyalgia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

  本发明涉及取代芳基环烷酰衍生物、含有这些衍生物的组合物以及它们的使用方法，用于预防和治疗由单胺摄取改善的症状，包括但不限于血管运动症状（VMS）、性功能障碍、胃肠和泌尿系统疾病、慢性疲劳综合征、纤维肌痛综合征、神经系统疾病和其组合，特别是选择自主神经失调症、血管运动症状、压力和切迫性尿失禁、纤维肌痛、疼痛、糖尿病神经病变以及其组合的病症。
• WHITE ROT FUNGUS AND METHOD FOR DEGRADING DIOXINS BY USING THE SAME
  申请人：Wakao Construction Co., Ltd.

  公开号：EP1114680A1

  公开（公告）日：2001-07-11

  White rot fungi capable of decomposing dioxin were screened from rotten wood to isolate the MZ-340 strain. This MZ-340 could be cultured in the Kirk liquid medium (HCLN) or PDB medium. New systems that can be used to decompose dioxins in incineration ash were constructed using this MZ-340 strain. The present invention can decompose dioxins in incineration ash effectively and efficiently in both solid phase systems and liquid phase systems. Thus, the present invention enables the prevention of environmental pollution by dioxins generated during incineration and also the clean up of dioxin pollutants.

  从朽木中筛选出能够分解二恶英的白腐真菌，并分离出 MZ-340 菌株。这种 MZ-340 菌株可在 Kirk 液体培养基（HCLN）或 PDB 培养基中培养。利用该 MZ-340 菌株构建了可用于分解焚烧灰中二恶英的新系统。本发明在固相系统和液相系统中都能有效和高效地分解焚烧灰中的二恶英。因此，本发明可以防止焚烧过程中产生的二恶英对环境造成污染，还可以清除二恶英污染物。