2,3,7,8-tetrachlorodibenzothiophene | 133513-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,3,7,8-tetrachlorodibenzothiophene
• 英文别名: 2,3,7,8-tetrachlorodibenzothiophen
• CAS: 133513-17-4
• 化学式: C₁₂H₄Cl₄S
• 分子量: 322.042
• InChiKey: GIMOCSHBYLEEKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  17
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3,4,4-四氯联苯 在 三氯化铝 、 sulfur 、 2,3,3',4-四氯联苯 作用下， 反应 10.0h， 生成 2,3,7,8-tetrachlorodibenzothiophene
  参考文献：
  名称：

  Sulfur analogues of polychlorinated dibenzo-P-dioxins, dibenzofurans and diphenyl ethers as inducers of CYP1A1 in mouse hepatoma cell culture and structure-activity relationships

  摘要：

  AbstractThree sulfur containing compounds, 2,3,7,8 tetrachlorothianthrene (TCTA), 2,3,7,8 tetrachlorodibenzothiophene (TCDT), and 3,3,4,4 tetrachlorodiphenyl sulfide (TCDPS), were analyzed for their CYP1A1 inducing potencies – measured as aryl hydrocarbon hydroxylase (AHH) and 7 ethoxyresorufin O‐deethylase (EROD) activities – in mouse hepatoma cell culture Hepa 1 Marked differences in the induction potencies were observed among the three compounds studied and between 2,3,7,8 tetrachlorodibenzo p dioxin (TCDD) and its sulfur analogue The estimated EC50 values for TCDD, TCTA, and TCDT were about 8 pM, 700 pM, and 7 5 nM, respectively TCDPS did not elicit any AHH/EROD induction Comparative molecular field analysis (CoMFA) was not able to predict correctly the biological potency of TCTA and TCDT The most important reason for the poor performance of the model may be the positive point charge of sulfur in TCTA and TCDT

  DOI：

  10.1002/etc.5620130917

文献信息

• Verfahren zur Herstellung von 2-Chlor-4-nitro-alkylbenzol
  申请人：BAYER AG

  公开号：EP0399293A1

  公开（公告）日：1990-11-28

  Bei der Herstellung von 2-Chlor-4-nitro-alkylbenzol durch Umsetzung von 4-Nitro-alkylbenzol mit elementarem Chlor oder Chlor abgebenden Verbindungen in Gegenwart eines Friedel-Crafts-Katalysators in flüssiger Phase werden besonders hohe Selektivitäten bezüglich der aus­schließlich in 2-Position chlorierten Zielverbindungen erreicht, wenn als Co-Katalysator ein dibenzokonden­sierter Schwefelheterocyclus der Formel mit den in der Beschreibung angegebenen Bedeutungen für R¹ bis R⁸, X und n eingesetzt wird.

  在液相中，在弗里德尔-卡夫斯催化剂存在下，通过 4-硝基烷基苯与元素氯或供氯 化合物反应制备 2-氯-4-硝基烷基苯时，如果使用式如下的二苯并缩硫杂环作为助催 化剂，则对完全在 2 位氯化的目标化合物具有特别高的选择性 式中 R¹至 R⁸、X 和 n 的含义在描述中给出。
• BUSER, HANS-RUDOLF;RAPPE, CHRISTOFFER, ANAL. CHEM., 63,(1991) N3, C. 1210-1217
  作者：BUSER, HANS-RUDOLF、RAPPE, CHRISTOFFER

  DOI：——

  日期：——
• Kopponen Paeivi, Sinkkonen Seija, Poso Antti, Gynther Jukka, Kaerenlampi +, Environ. Toxicol. and Chem., 13 (1994) N 9, S 1543-1548
  作者：Kopponen Paeivi, Sinkkonen Seija, Poso Antti, Gynther Jukka, Kaerenlampi +

  DOI：——

  日期：——
• US5095157A
  申请人：——

  公开号：US5095157A

  公开（公告）日：1992-03-10
• Sulfur analogues of polychlorinated dibenzo-<i>P</i>-dioxins, dibenzofurans and diphenyl ethers as inducers of CYP1A1 in mouse hepatoma cell culture and structure-activity relationships
  作者：Paivi Kopponen、Seija Sinkkonen、Antti Poso、Jukka Gynther、Sirpa Karenlampi

  DOI：10.1002/etc.5620130917

  日期：1994.9

  AbstractThree sulfur containing compounds, 2,3,7,8 tetrachlorothianthrene (TCTA), 2,3,7,8 tetrachlorodibenzothiophene (TCDT), and 3,3,4,4 tetrachlorodiphenyl sulfide (TCDPS), were analyzed for their CYP1A1 inducing potencies – measured as aryl hydrocarbon hydroxylase (AHH) and 7 ethoxyresorufin O‐deethylase (EROD) activities – in mouse hepatoma cell culture Hepa 1 Marked differences in the induction potencies were observed among the three compounds studied and between 2,3,7,8 tetrachlorodibenzo p dioxin (TCDD) and its sulfur analogue The estimated EC50 values for TCDD, TCTA, and TCDT were about 8 pM, 700 pM, and 7 5 nM, respectively TCDPS did not elicit any AHH/EROD induction Comparative molecular field analysis (CoMFA) was not able to predict correctly the biological potency of TCTA and TCDT The most important reason for the poor performance of the model may be the positive point charge of sulfur in TCTA and TCDT