2,4-dichloroestrone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2,4-dichloroestrone
• 英文别名: (8R,9S,13S,14S)-2,4-dichloro-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• 化学式: C₁₈H₂₀Cl₂O₂
• 分子量: 339.262
• InChiKey: KOLZHBONHHHUMH-HIONPOMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dichloroestrone 、 甲醇 在 sodium hypochlorite 作用下， 反应 0.5h， 以8.9 mg的产率得到2,4,10-trichloro-1,4-estradiene-3,17-dione
  参考文献：
  名称：

  Formation of chlorinated estrones via hypochlorous disinfection of wastewater effluent containing estrone

  摘要：

  Chlorinated derivatives of estrone (E1) in the effluent of a municipal sewage treatment plant located in Shizuoka prefecture, Japan were detected by gas chromatography/mass spectrometry using electron impact in selected ion monitoring (GC/MS-E1-SIM) analysis. The concentrations of E1, 2-chloroestrone, 4-chloroestrone and 2,4-dichloroestrone in the effluent sample collected in December 2005 were 60.0 ng l(-1), 4.0 ng l(-1), 14.5 ng l(-1), and 9.8 ng l(-1), respectively. In the effluent sample taken in June 2005, 2,4-dichloroestrone was detected at 5.6 ng l(-1) along with 17.6 ng l(-1) of E1. However, only E1 was detected at 5.9 ng l(-1) in the sample in May 2005. To elucidate the behavior of E1 during the disinfection process with sodium hypochlorite in the sewage treatment plant, we carried out a reaction of E1 with sodium hypochlorite in buffer solutions at pH 7 and 9. As E1 was consumed rapidly, chlorinated estrones were produced and relatively fast formation of 2-chloroestrone, 4-chloroestrone, and 2,4-dichloroestrone was observed. Furthermore, 1,4-estradiene-3,17-dione derivatives were formed from the reaction between 2,4-dichloroestrone and sodium hypochlorite. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.chemosphere.2006.09.011
• 作为产物：
  描述：

  雌酚酮 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到4-chloroestrone
  参考文献：
  名称：

  作为雌激素生物合成酶抑制剂的2-和/或4-卤代13β-和13α-雌酮衍生物的合成及其构效关系。

  摘要：

  合成了具有N-卤代琥珀酰亚胺作为亲电子引发剂的A环卤代13α-，13β-和17-脱氧13α-雌酮衍生物。取代发生在位置C-2和/或C-4。通过体外放射性底物孵育研究了卤代雌酮对人芳香酶，类固醇硫酸酯酶或17β-羟基类固醇脱氢酶1活性的潜在抑制作用。潜在的亚微摩尔或低微摩尔抑制剂具有偶发的双重或多重抑制特性。通过获得的抑制数据的比较，建立了重要的构效关系。

  DOI：

  10.1080/14756366.2018.1490731

文献信息

• Products of Aqueous Chlorination of 17β-Estradiol and Their Estrogenic Activities
  作者：Jianying Hu、Shuijie Cheng、Takako Aizawa、Yoshiyasu Terao、Shoichi Kunikane

  DOI：10.1021/es034324+

  日期：2003.12.1

  To assess the estrogenic activity potentially stemming from 17beta-estradiol (E2) in drinking water, ESI-LC-MS was used to identify the products of its aqueous chlorination under the following conditions: 50 mug/L E2, 1.46 mg/L sodium hypochlorite, pH 7.5, 25 degreesC. Seven products, including 2,4-dichloro-17beta-estradiol, monochloroestrone, 2,4-dichloroestrone, and the four byproducts such as 4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7alpha-methyloctahydroinden-5-one (product C in the text) were identified in chlorinated E2 solution. The estrogenic activities of the aqueous chlorinated E2 solution at 10, 30, 60, 120, and 180 min contact time were assessed by a yeast two-hybrid system based on the ligand-dependent interaction of two proteins, a human estrogen receptor (ER) and a coactivator. All five solutions elicited transcriptional activation induction. The maximal beta-galactosidase activities induced by the chlorinated solution at 10, 30, and 60 min were similar and slightly lower than those before chlorination, while the activities of the chlorinated solution at 120 and 180 min were about 40% of those before chlorination. Finally, 4-chloro-17beta-estradiol (4-chloro-E2) (we failed to synthesize the 2-chloroestrone (2-chloro-E1)), 2,4-dichloro-17beta-estradiol (2,4-dichloro-E2), and 2,4-dichloroestrone (2,4-dichloro-E1) were synthesized, and product C was fractionated by HPLC. It was found that 4-chloro-E2 elicited strong estrogenic activity, at almost the same level as that of estrone (EC50 = 10(2) nM), while 2,4-dichloro-E2 elicited weaker beta-galactosidase activity compared with that of 4-chloro-E2. The EC50 was ca. 10(3) nM. The maximal beta-galactosidase activity for 2,4-dichloro-E1 was lower than that of 2,4-dichloro-E2, while its EC50 was similar to that of 2,4-dichloro-E2. In addition, product C, 4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7alpha-methyloctahydroinden-5-one, induced high beta-galactosidase activity at the relatively higher concentration of 3.5 x 10(5) nM. On the basis of the dose-response curve of a single byproduct of chlorinated E2, the estrogenic activity 120 and 180 min appears to be induced mainly by 2,4-dichloro-E2 and 2,4-dichloro-E1.