2-chloro-17α-ethynylestradiol | 137576-28-4

• 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-chloro-17α-ethynylestradiol
• 英文别名: 2-chloro-17α-ethynyl-17β-estradiol；2-chloroethinylestradiol；(8R,9S,13S,14S,17R)-2-chloro-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 137576-28-4
• 化学式: C₂₀H₂₃ClO₂
• 分子量: 330.854
• InChiKey: ZHZAMHPIHLQROO-BKRJIHRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-chloroestrone 、 lithium acetylide-ethylenediamine complex 以 二甲基亚砜 为溶剂， 以78%的产率得到2-chloro-17α-ethynylestradiol
  参考文献：
  名称：

  Ali, Hasrat; Lier, Johan E. van, Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2485 - 2491

  摘要：

  DOI：

文献信息

• Effect of 11β-substituents on the regioselective chlorination of estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone
  作者：Hasrat Ali、Johan E. van Lier

  DOI：10.1016/0039-128x(94)90065-5

  日期：1994.8

  The reaction of 11 beta-substituted estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone affords exclusively ortho-substituted monochlorinated products including a major 4-chloro and a minor 2-chloro derivative. In the absence of an 11 beta-substituent, regioselectivity is lost, resulting in a mixture of 10 beta- and ortho-chlorinated products.
• Efficient Removal of Estrogenic Activity during Oxidative Treatment of Waters Containing Steroid Estrogens
  作者：Yunho Lee、Beate I. Escher、Urs von Gunten

  DOI：10.1021/es7023302

  日期：2008.9.1

  The discharge of synthetic and natural steroid estrogens from municipal wastewaters to the aquatic environment has received increased attention because of their potential reproductive effects on fish. Using 17 alpha-ethinylestradiol (EE2) as a representative steroid estrogen, several oxidants applied in wastewater treatment (chlorine, bromine, ozone, hydroxyl radical, chlorine dioxide, and ferrate) were shown to selectively and rapidly transform EE2. For typically applied oxidant doses, these transformations occur in the time range of seconds to minutes. The resulting initial transformation products of EE2 exhibit a substantially lower in vitro estrogenic activity (< 13% of EE2). For selected structural derivatives of EE2, a quantitative structure-activity relationship was established between substituents changed on the phenolic moiety and the relative in vitro estrogenic activity. In addition,the initial EE2 transformation products that still exhibit residual estrogenic activity are quickly further transformed by most of the tested oxidants. Therefore, oxidative wastewater treatment may serve as a powerful tool to remove estrogenic activity induced by steroid estrogens.