4-methylene-4,5-secocholestane | 140183-67-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-methylene-4,5-secocholestane
• CAS: 140183-67-1
• 化学式: C₂₈H₅₀
• 分子量: 386.705
• InChiKey: COVJLAWTXUOGSB-ZYEPEFIZSA-N

物化性质

• 沸点：
  447.1±12.0 °C(predicted)
• 密度：
  0.872±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.05
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-methylene-4,5-secocholestane 在 镍 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以19 mg的产率得到4-methyl-4,5-secocholestane
  参考文献：
  名称：

  Studies of the synthesis of biomarkers. XI. Synthesis of 4,5-secocholestane and 4-methyl-4,5-secocholestane

  摘要：

  4,5-Secocholestane (1a) and 4-methyl-4,5-secocholestane (1b) were synthesized from cholesterol (2) in five and seven steps, respectively. The key intermediate, 5-oxo-4,5-secocholestan-4-al (7) was reduced by the Clemmensen method to afford 1a. Meanwhile, 7 underwent selective Wittig reaction, Clemmensen reduction, and hydrogenation to give another target molecule, 1b. The structure of an unknown biomarker was shown to be different from the proposed 1a by gas chromatographic and mass spectrometric comparison.

  DOI：

  10.1016/0039-128x(92)90024-4
• 作为产物：
  描述：

  5-oxo-4,5-secocholestan-4-al 在 盐酸 、 汞 、 锌 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 7.5h， 生成 4-methylene-4,5-secocholestane
  参考文献：
  名称：

  Studies of the synthesis of biomarkers. XI. Synthesis of 4,5-secocholestane and 4-methyl-4,5-secocholestane

  摘要：

  4,5-Secocholestane (1a) and 4-methyl-4,5-secocholestane (1b) were synthesized from cholesterol (2) in five and seven steps, respectively. The key intermediate, 5-oxo-4,5-secocholestan-4-al (7) was reduced by the Clemmensen method to afford 1a. Meanwhile, 7 underwent selective Wittig reaction, Clemmensen reduction, and hydrogenation to give another target molecule, 1b. The structure of an unknown biomarker was shown to be different from the proposed 1a by gas chromatographic and mass spectrometric comparison.

  DOI：

  10.1016/0039-128x(92)90024-4