1,7-二氯二苯并呋喃 | 94538-02-0

• 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: 1,7-二氯二苯并呋喃
• 英文名称: 1,7-dichlorodibenzofuran
• CAS: 94538-02-0
• 化学式: C₁₂H₆Cl₂O
• 分子量: 237.085
• InChiKey: XRQNHPGZRFKBJW-UHFFFAOYSA-N

物化性质

• 保留指数：
  1908;1910;1910

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 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（多氯二苯并呋喃PCDFs和多溴二苯并呋喃PBDFs）与芳烃受体（AhR）结合，增强了其激活XRE（外源性生物响应元件）启动子区域的转录能力。特别是AhR与PCDF结合后，将其转移到细胞核中，并与芳烃核转运蛋白（ARNT）和外来物响应元件（XRE）一起增加了CYP1A1和芳烃羟化酶（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-连环蛋白信号通路，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酶体降解，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的人群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

• 作为反应物：
  描述：

  1,7-二氯二苯并呋喃 、 苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以65%的产率得到1-chloro-7-phenyldibenzo[b,d]furan
  参考文献：
  名称：

  COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE, AND DISPLAY DEVICE

  摘要：

  一种用于有机光电器件的化合物，包括该化合物的有机光电器件组成，有机光电器件和显示器件，该化合物由化学式1和化学式2的组合表示。

  公开号：

  US20220140257A1
• 作为产物：
  描述：

  3-氯苯酚 在 silica gel 、 copper dichloride 作用下， 生成 邻氯苯酚 、 3,7-二氯二苯并呋喃 、 1,7-二氯二苯并呋喃 、 1,9-dichlorodibenzo-p-dioxin
  参考文献：
  名称：

  Temperature dependence of DCDD/F isomer distributions from chlorophenol precursors

  摘要：

  The temperature dependence of the gas-phase, rate-limited formation of dichlorodibenzo-p-dioxin (DCDD) and dichlorodibenzofuran (DCDF) isomers from 2,6-dichlorophenol and 3-chlorophenol, respectively, has been studied experimentally in an isothermal flow reactor over the range 300-900 degreesC under pyrolytic, oxidative and catalytic conditions and computationally using semi-empirical molecular orbital methods. At high temperatures, distributions of sets of DCDD/F condensation products are consistent with the calculated thermodynamic distributions, indicating that the relative rates of formation are governed by differences in symmetry and steric hindrance present in the isomer product structures. At low temperatures, however, this is not the case. In the case of 1,6- and 1,9-DCDD formed from 2, 6-dichlorophenol via Smiles rearrangement, the 1,6 isomer is favored at low temperatures more than thermodynamically predicted. This result appears to be consistent with kinetic effects of either the expansion of the five-membered ring Smiles intermediate or a lower activation energy six-membered ring intermediate pathway that produces only the 1,6 isomer. For formation of 1,7-, 3,7- and 1,9-DCDF from 3-chlorophenol, the 1,7 isomer fraction increases at low temperatures whereas thermodynamics predicts a decrease. This result can be attributed to steric effects in alternative "sandwich-type" approach geometries of phenoxy radicals to form the o, o'-dihydroxybiphenyl (DOHB) intermediate via its keto-tautomers. Higher level molecular theory (ab initio) is needed to provide a more quantitative description of these kinetics. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0045-6535(00)00246-0

文献信息

• Formation of chlorinated phenols, dibenzo-p-dioxins, dibenzofurans, benzenes, benzoquinnones and perchloroethylenes from phenols in oxidative and copper (II) chloride-catalyzed thermal process
  作者：Jae-Yong Ryu

  DOI：10.1016/j.chemosphere.2007.10.036

  日期：2008.4

  CuCl(2). Chlorination preferentially occurred on ortho-(2, 6) and para-(4) positions. Chlorination increased up to 200 degrees C, and thereafter decreased as temperature increased. Chlorination of phenols plays an important role in the formation of the more chlorinated PCDD/Fs. Chlorinated benzenes are formed possibly from both chlorination of benzene and chlorodehydroxylation of phenols. Chlorinated phenols

  在100-425℃的温度范围内，在流式反应器中研究了CuCl（2）上由未取代苯酚和三种一氯酚形成多氯二苯对恶二恶英（PCDDs），多氯二苯并呋喃（PCDFs）和氯化苯酚。含8.0％氧气的氮气流用作载气。将0.00024摩尔未取代的苯酚和0.00039摩尔每种一氯苯酚通过1g和1cm的SiO（2）颗粒，其中包含0.5％（Cu质量）CuCl（2）。氯化反应优先发生在邻位（2，6）和对位（4）位置。氯化增加到200摄氏度，然后随温度升高而降低。苯酚的氯化在氯化程度更高的PCDD / Fs的形成中起着重要作用。氯化苯可能是由苯的氯化和苯酚的氯脱羟基化而形成的。带有邻氯的氯化苯酚形成PCDD产物，而主要的PCDD产物是通过损失一个氯而生产的。对于PCDF的形成，至少需要一种未氯化的原碳。
• HETEROCYCLIC COMPOUNDS COMPRISING DIBENZOFURAN AND/OR DIBENZOTHIOPHENE STRUCTURES
  申请人：Merck Patent GmbH

  公开号：US20190165282A1

  公开（公告）日：2019-05-30

  The present invention describes dibenzofuran and dibenzothiophene derivatives substituted by electron-transporting groups, especially for use as triplet matrix materials in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.
• [DE] HETEROCYCLISCHE VERBINDUNGEN MIT DIBENZOFURAN- UND/ODER DIBENZOTHIOPHEN-STRUKTUREN<br/>[EN] HETEROCYCLIC COMPOUNDS COMPRISING DIBENZOFURAN AND/OR DIBENZOTHIOPHENE STRUCTURES<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES À STRUCTURES DIBENZOFURANES ET/OU DIBENZOTHIOPHÈNES
  申请人：MERCK PATENT GMBH

  公开号：WO2017178311A1

  公开（公告）日：2017-10-19

  Die vorliegende Erfindung beschreibt Dibenzofuran-und Dibenzothiophen-derivate, welche mit elektronentransportierenden Gruppen substituiert sind, insbesondere zur Verwendung als Triplettmatrixmaterialien in elektronische Vorrichtungen. Die Erfindung betrifft ferner ein Verfahren zur Herstellung der erfindungsgemäßen Verbindungen sowie elektronische Vorrichtungen, enthaltend diese.
• Temperature dependence of DCDD/F isomer distributions from chlorophenol precursors
  作者：James A. Mulholland、Umesh Akki、Yun Yang、Jae-Yong Ryu

  DOI：10.1016/s0045-6535(00)00246-0

  日期：2001.2

  The temperature dependence of the gas-phase, rate-limited formation of dichlorodibenzo-p-dioxin (DCDD) and dichlorodibenzofuran (DCDF) isomers from 2,6-dichlorophenol and 3-chlorophenol, respectively, has been studied experimentally in an isothermal flow reactor over the range 300-900 degreesC under pyrolytic, oxidative and catalytic conditions and computationally using semi-empirical molecular orbital methods. At high temperatures, distributions of sets of DCDD/F condensation products are consistent with the calculated thermodynamic distributions, indicating that the relative rates of formation are governed by differences in symmetry and steric hindrance present in the isomer product structures. At low temperatures, however, this is not the case. In the case of 1,6- and 1,9-DCDD formed from 2, 6-dichlorophenol via Smiles rearrangement, the 1,6 isomer is favored at low temperatures more than thermodynamically predicted. This result appears to be consistent with kinetic effects of either the expansion of the five-membered ring Smiles intermediate or a lower activation energy six-membered ring intermediate pathway that produces only the 1,6 isomer. For formation of 1,7-, 3,7- and 1,9-DCDF from 3-chlorophenol, the 1,7 isomer fraction increases at low temperatures whereas thermodynamics predicts a decrease. This result can be attributed to steric effects in alternative "sandwich-type" approach geometries of phenoxy radicals to form the o, o'-dihydroxybiphenyl (DOHB) intermediate via its keto-tautomers. Higher level molecular theory (ab initio) is needed to provide a more quantitative description of these kinetics. (C) 2001 Elsevier Science Ltd. All rights reserved.
• COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE, AND DISPLAY DEVICE
  申请人：SAMSUNG SDI CO., LTD.

  公开号：US20220140257A1

  公开（公告）日：2022-05-05

  A compound for an organic optoelectronic device, a composition for an organic optoelectronic device including the same, an organic optoelectronic device, and a display device, the compound being represented by a combination of Chemical Formula 1 and Chemical Formula 2,

  一种用于有机光电器件的化合物，包括该化合物的有机光电器件组成，有机光电器件和显示器件，该化合物由化学式1和化学式2的组合表示。