3-氯双酚A | 74192-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氯双酚A
• 英文名称: 3-Chlorobisphenol A
• 英文别名: 2-(3-chloro-4-hydroxyphenyl)-(4-hydroxyphenyl)propane；3-monochlorobisphenol A；monochlorobisphenol A；2-chlorobisphenol A；tetrachlorobisphenol A；bisphenol Cl；2-chloro-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
• CAS: 74192-35-1
• 化学式: C₁₅H₁₅ClO₂
• 分子量: 262.736
• InChiKey: XLRAFMYRFQJARM-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  165 °C(Press: 0.05 Torr)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、乙酸乙酯（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  双酚A 在 sodium hypochlorite 、 二乙烯三胺五醋酸 、 次氯酸 作用下， 以 甲醇 、 aq. phosphate buffer 、 水 为溶剂， 以51%的产率得到3-氯双酚A
  参考文献：
  名称：

  Molecular docking of bisphenol A and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma

  摘要：

  A xenoestrogen and known endocrine disruptor, bisphenol A (BPA) binds the human estrogen-related receptor-gamma (ERR gamma) with high affinity (Kd approximate to 5.5 nM). It is likely that BPA undergoes oxidative biotransformation by hypochlorite/hypochlorous acid (-OCl/HOCl) and peroxynitrite (PN) and the products formed in these reactions may serve as secondary estrogens and contribute to the toxicodynamics of BPA. Therefore, in the present study we have examined the formation of chlorinated and nitrated BPA in reactions of BPA with -OCl/HOCl and PN(+CO2) performed around the neutral pH. We have identified four major products in these reactions and they include 3-chloro-BPA (CBPA), 3,3'-dichloro-BPA (DCBPA), 3-nitro-BPA (NBPA) and 3,3'-dinitro-BPA (DNBPA). Towards understanding the toxicodynamics and estrogenic activity of BPA in biological systems, we have performed molecular docking of BPA, CBPA, DCBPA, DNBPA and NBPA onto the ERR gamma using AutoDock 4.2 software and compared the binding energies with those of estradiol, the natural ligand. Based on the genetic algorithm, the three best conformations were selected and averaged for each ligand and a detailed analysis of molecular interactions based on free energies of binding (kcal/mol) was computed. The results indicate the following rank order of binding to ERR gamma: BPA (-8.78 +/- 0.06) > CBPA (-8.53 +/- 0.41) > NBPA (-7.36 +/- 0.74) > DCBPA (-5.24 +/- 0.17) > DNBPA (-4.95 +/- 0.78) > estradiol (-4.94 +/- 1.04). The docking studies revealed that the OH group of one of the phenyl rings forms a hydrogen bond with Glu275/Arg316, while the OH group of other phenyl ring was bound to Asp346. These results suggest that both BPA and its putative chlorinated and nitrated metabolites have strong binding affinity compared to estradiol. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2012.08.065

文献信息

• [EN] ANDROGEN RECEPTOR MODULATORS AND METHODS FOR USE AS PROTEOLYSIS TARGETING CHIMERA LIGANDS<br/>[FR] MODULATEURS DU RÉCEPTEUR DES ANDROGÈNES ET MÉTHODES ASSOCIÉES À UTILISER EN TANT QUE LIGANDS CHIMÈRES CIBLANT LA PROTÉOLYSE
  申请人：ESSA PHARMA INC

  公开号：WO2020198711A1

  公开（公告）日：2020-10-01

  The present invention relates to bifunctional Proteolysis Targeting Chimeric ligands (Protac compounds) comprising a ligase modulator/binder and a molecule that binds to a protein target of interest, and methods of treating various diseases and conditions with the Protac compounds, including diseases associated with androgen receptors.

  本发明涉及双功能蛋白水解靶向嵌合配体（Protac化合物），包括一个连接酶调节剂/结合物和一个结合到感兴趣的蛋白靶标的分子，以及使用Protac化合物治疗各种疾病和病况的方法，包括与雄激素受体相关的疾病。
• ¹H and¹³C NMR spectral assignments of halogenated transformation products of pharmaceuticals and related environmental contaminants
  作者：Kemal Solakyildirim、Daryl N. Bulloch、Cynthia K. Larive

  DOI：10.1002/mrc.4056

  日期：2014.6

  ion often present in wastewaters. Analytical standards of most halogenated PPCP TPs are unavailable, necessitating their synthesis and purification. This study focuses on the NMR characterization of the major chlorination products of a set of parent PPCPs selected because of their documented presence in wastewater effluents, potential for halogenation under conditions employed in wastewater treatment

  药品和个人护理产品 (PPCP) 是一类新兴的环境污染物，在废水中经常遇到 ng-μg/L 水平。一些 PPCP 已引起监管部门对其在环境中的存在的担忧，因为它们能够对非目标水生生物群产生内分泌干扰影响。最近的研究表明，当常用消毒剂氯（通常以次氯酸钠形式引入）在污水排放之前应用时，PPCP 有可能在废水处理过程中被氯化，从而产生通常称为转化产物 (TP) 的卤化消毒副产物。这些化合物可以通过氧化废水中经常存在的溴离子进行氯化或溴化。大多数卤化 PPCP TP 的分析标准品不可用，需要它们的合成和纯化。本研究的重点是对一组母体 PPCP 的主要氯化产物进行 NMR 表征，因为它们记录在废水流出物中，在废水处理所采用的条件下可能发生卤化，以及对于一些 PPCP，其毒理学特性父 PPCP 或其 TP。水杨酸是镇痛药乙酰水杨酸的代谢物，其二氯化 TP 已被鉴定为 20α 羟基类固醇脱氢酶的有效抑制
• Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants
  作者：Hitoshi Fukazawa、Kentaro Hoshino、Tatsushi Shiozawa、Hidetsuru Matsushita、Yoshiyasu Terao

  DOI：10.1016/s0045-6535(00)00507-5

  日期：2001.8

  Chlorinated derivatives of bisphenol A were detected in the final effluents of eight paper manufacturing plants in Shizuoka, Japan, where thermal paper and/or other printed paper is used as the raw material. Their amounts were determined by gas chromatography/mass spectrometry (GC/MS) after treatment with N,O-bis(trimethylsilyl)trifluoroacetamide, and ranged from traces to 2.0 mug/l. They are likely produced by chlorination of bisphenol A, which was released into the effluents from the pulping process of wastepaper, during or after bleaching with chlorine. (C) 2001 Elsevier Science Ltd. All rights reserved.
• US4195157A
  申请人：——

  公开号：US4195157A

  公开（公告）日：1980-03-25
• US4210765A
  申请人：——

  公开号：US4210765A

  公开（公告）日：1980-07-01

表征谱图