5β-chola-1,7-dien-3α,24-diol

• 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: 5β-chola-1,7-dien-3α,24-diol
• 英文别名: (3S,5R,9S,10R,13R,14R,17R)-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-4,5,6,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₄H₃₈O₂
• 分子量: 358.565
• InChiKey: ATZOXJCRZGMDEK-DHEFEZHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  鹅去氧胆酸 在 铂 吡啶 、 盐酸 、 氧气 、 phenyltrimethylammonium tribromide 、 lithium carbonate 、 二异丁基氢化铝 、 lithium bromide 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 118.42h， 生成 5β-chola-1,7-dien-3α,24-diol
  参考文献：
  名称：

  Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis

  摘要：

  We have synthesized a tritiated form of 5beta-cholest-7-ene-3,6-dione (5beta-diketone) of high specific activity (9.2 TBq/mmol) in ten steps from deoxychenocholic acid, which possesses the desired A/B cis ring junction (5beta-H configuration). We have conceived a synthetic pathway which permits labelling by tritiation at the final step and allowing for the introduction of the tritium label into both the side chain and the nucleus. We have examined the ability of insect endocrine glands (prothoracic glands) of Pieris Brassicae to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. No conversion can be detected. In the myriapod Lithobius forficatus only reduction of the 3-ketone can be observed. It seems that the 5beta-diketone is not an intermediate in the ecdysone biosynthetic pathway.

  DOI：

  10.1016/s0040-4020(01)86327-4

文献信息

• Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis
  作者：Frédéric Dolle、Charles Hetru、Bernard Rousseau、Frank Sobrio、Catherine Blais、René Lafont、Michel Descamp、Bang Luu

  DOI：10.1016/s0040-4020(01)86327-4

  日期：1993.3

  We have synthesized a tritiated form of 5beta-cholest-7-ene-3,6-dione (5beta-diketone) of high specific activity (9.2 TBq/mmol) in ten steps from deoxychenocholic acid, which possesses the desired A/B cis ring junction (5beta-H configuration). We have conceived a synthetic pathway which permits labelling by tritiation at the final step and allowing for the introduction of the tritium label into both the side chain and the nucleus. We have examined the ability of insect endocrine glands (prothoracic glands) of Pieris Brassicae to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. No conversion can be detected. In the myriapod Lithobius forficatus only reduction of the 3-ketone can be observed. It seems that the 5beta-diketone is not an intermediate in the ecdysone biosynthetic pathway.