5α-cholesta-8,14-dien-3α-ol | 206058-57-3

• 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: 5α-cholesta-8,14-dien-3α-ol
• 英文别名: (3R,5S,10S,13R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 206058-57-3
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: AWBZPJQUWZBRII-RLFKVNLLSA-N

物化性质

• 沸点：
  498.6±44.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5α-cholesta-8,14-dien-3α-ol 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 以7.5%的产率得到3β-fluoro-5α-cholesta-8,14-diene
  参考文献：
  名称：

  Synthesis of Meiosis-Activating Sterols Containing Fluorine.

  摘要：

  It is documented that specific types of sterol play a major role in the resumption of meiosis in oocytes from mice in vitro. 4,4-Dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol (FF-MAS) isolated from human follicular fluid and 4,4-dimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol (T-MAS) isolated from bull testicular tissue, have been shown to activate (promote) meiosis in vitro. In order to evaluate the biological activity and stability of such compounds, new demethylsterol derivatives have been synthesised. Using diethylaminosulfur trifluoride (DAST) it was possible to synthesise selected Delta(8), Delta(14) sterols with mono and difluoro substitution at C3.

  DOI：

  10.3891/acta.chem.scand.52-0503
• 作为产物：
  描述：

  5α-cholesta-8,14-dien-3β-ol 在 sodium hydroxide 、 双氧水 、 aluminum isopropoxide 、 lithium tri-sec-butyl(hydrido)borate 、 丁酮 作用下， 反应 0.2h， 生成 5α-cholesta-8,14-dien-3α-ol
  参考文献：
  名称：

  Synthesis of Meiosis-Activating Sterols Containing Fluorine.

  摘要：

  It is documented that specific types of sterol play a major role in the resumption of meiosis in oocytes from mice in vitro. 4,4-Dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol (FF-MAS) isolated from human follicular fluid and 4,4-dimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol (T-MAS) isolated from bull testicular tissue, have been shown to activate (promote) meiosis in vitro. In order to evaluate the biological activity and stability of such compounds, new demethylsterol derivatives have been synthesised. Using diethylaminosulfur trifluoride (DAST) it was possible to synthesise selected Delta(8), Delta(14) sterols with mono and difluoro substitution at C3.

  DOI：

  10.3891/acta.chem.scand.52-0503

文献信息

• Synthesis of Meiosis-Activating Sterols Containing Fluorine.
  作者：Martin Wenckens、Frederik Grønvald、John Bondo Hansen、Olle Matsson、Jadwiga Trocha-Grimshaw、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0503

  日期：——

  It is documented that specific types of sterol play a major role in the resumption of meiosis in oocytes from mice in vitro. 4,4-Dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol (FF-MAS) isolated from human follicular fluid and 4,4-dimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol (T-MAS) isolated from bull testicular tissue, have been shown to activate (promote) meiosis in vitro. In order to evaluate the biological activity and stability of such compounds, new demethylsterol derivatives have been synthesised. Using diethylaminosulfur trifluoride (DAST) it was possible to synthesise selected Delta(8), Delta(14) sterols with mono and difluoro substitution at C3.