(2Z,2'Z)-2,2'-((3R,3aS,5aS,9aR,9bS)-3-ethynyl-3-hydroxy-3a-methyldecahydro-1H-cyclopenta[a]naphthalene-6,7-diylidene)diacetic acid | 1006654-79-0

• 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: (2Z,2'Z)-2,2'-((3R,3aS,5aS,9aR,9bS)-3-ethynyl-3-hydroxy-3a-methyldecahydro-1H-cyclopenta[a]naphthalene-6,7-diylidene)diacetic acid
• CAS: 1006654-79-0
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GZXBBKJVNUCJAG-QSQXSQGISA-N

物化性质

• 沸点：
  539.2±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  94.83
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  炔雌醇 在 臭氧 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成 (2Z,2'Z)-2,2'-((3R,3aS,5aS,9aR,9bS)-3-ethynyl-3-hydroxy-3a-methyldecahydro-1H-cyclopenta[a]naphthalene-6,7-diylidene)diacetic acid 、 、 、 、 、 、 2-羟基炔雌醇
  参考文献：
  名称：

  Ozonation of ethinylestradiol in aqueous-methanolic solution: direct monitoring by electrospray ionization mass spectrometry

  摘要：

  The ozonolysis of ethinylestradiol (1), a synthetic steroidal estrogen, in an aqueous-methanolic solution was investigated. HPLC-UV analyses revealed that 1 was completely consumed after a 20 min reaction time either at pH 5 or 8. ESI(-)-MS (electrospray ionization mass spectrometry in the negative ion mode) monitoring also revealed the continuous consumption of 1 (detected as [1 - H](-) of m/z 295) concomitantly with the emergence of oxidation products. Chemical structures were proposed for these products based on the data of MS and MS/MS (the m/z values and fragmentation profiles of the anionic specie, respectively). These data, in conjunction with the well-established knowledge about the reactivity of organic molecules toward ozone in aqueous solution, were evaluated and an unprecedented reaction route for the ozonation of 1 could thus be suggested. Hence, the first step in this reaction sequence was ascribed to involve a 1,3-dipolar cycloaddition of ozone at the phenolic ring of 1 yielding the di-hydroxylated product 2 (detected as [2 - H](-) of m/z 311). The loss of acetylene as the unique dissociation channel for [2 - H](-) thus confirmed that such hydroxylation occurred at the phenolic ring rather than the acetylenic moiety of 1. Subsequent oxidations were proposed to be the origin of a number of other products, all of them bearing the COOH functionally (this was verified by the characteristic loss of CO2 during the dissociation of the related deprotonated molecules). The ESI(-)-MS records also revealed notable differences between the reaction conducted at pH 5 and 8, i.e. at slightly acid or basic media, respectively.

  DOI：

  10.1590/s0103-50532010000500004