4-chloro-17α-ethynylestradiol | 137576-16-0

• 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: 4-chloro-17α-ethynylestradiol
• 英文别名: 4-chloro-(17α)-19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol；4-chloro-17α-ethynyl-17β-estradiol；4-chloroethinylestradiol；(8R,9S,13S,14S,17R)-4-chloro-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 137576-16-0
• 化学式: C₂₀H₂₃ClO₂
• 分子量: 330.854
• InChiKey: OOIVVMYMQFWSGZ-RXUQYVRZSA-N

物化性质

• 沸点：
  464.1±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

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：

  (4-氯-13-甲基-3-氧代-2,6,7,8,9,10,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-17-基)乙酸酯 在 selenium(IV) oxide 、 jones' reagent 、 sodium carbonate 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 丙酮 、 叔丁醇 为溶剂， 反应 68.33h， 生成 4-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

• Identification and behavior of reaction products formed by chlorination of ethynylestradiol
  作者：Kenji Moriyama、Hiroshi Matsufuji、Makoto Chino、Mitsuharu Takeda

  DOI：10.1016/j.chemosphere.2003.11.045

  日期：2004.5

  Six products were formed by reaction of ethynylestradiol (EE2) with sodium hypochlorite in buffered solutions. 4-Chloroethynylestradiol (4-ClEE2) and 2,4-dichloroethynylestradiol (2,4-diClEE2) were identified as the two major reaction products, using preparative HPLC, MS, and NMR. When EE2 reacted with chlorine at different pHs (pH 5, 7, and 9) or chlorine concentrations (0.2, 1, 2, and 5 mmol/l, corresponding

  乙炔雌二醇（EE2）与次氯酸钠在缓冲溶液中反应生成六种产物。使用制备型HPLC，MS和NMR将4-氯代乙炔雌二醇（4-ClEE2）和2,4-二氯乙炔基雌二醇（2,4-diClEE2）鉴定为两种主要反应产物。当EE2与氯在不同pH（pH 5、7和9）或氯浓度（0.2、1、2和5 mmol / l）反应时，分别对应于EE2、1、5、10和25的摩尔比），在上述条件下观察到4-ClEE2和2,4-diClEE2的形成，最高产率分别为20和52mol％。通过添加大于1 mmol / l的氯（相对于EE2的摩尔比为5），在氯化的5分钟内EE2几乎被完全消耗掉。另一方面，两种产物在60分钟后仍存在于高度氯化的溶液中（4ClEE2，1-6 mol％; 2，4-diClEE 2，3-25 mol％）。用雌激素受体α或β结合试验测定4-ClEE2的雌激素活性与亲本EE2相似，而2,4-diClEE2的活性则低约10倍。
• 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.