5β-cholesta-1,7-diene-3,6-dione | 137204-86-5

• 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-cholesta-1,7-diene-3,6-dione
• CAS: 137204-86-5
• 化学式: C₂₇H₄₀O₂
• 分子量: 396.613
• InChiKey: IITNONGAYNNQPN-ZLNDANPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5β-cholesta-1,7-diene-3,6-dione 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以76%的产率得到14α-hydroxy-5β-cholesta-1,7-diene-3,6-dione
  参考文献：
  名称：

  Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis in Locusta migratoria

  摘要：

  We have synthesized a tritiated form of 14-alpha-hydroxy-5-beta-cholest-7-ene-3,6-dione (5-beta-diketol) of high specific activity (1.74 TBq/mmol) from 7-dehydrocholesterol in seven steps with stereoselective introduction of the A/B cis ring junction as the key reaction. We have examined the ability of endocrine glands (prothoracic glands) of Locusta migratoria to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. A very efficient conversion of 5-beta-diketol to ecdysone and to 3-dehydroecdysone was monitored, which opens up new possibilities for the understanding of the role of 3-dehydro-compounds in ecdysteroid biosynthesis.

  DOI：

  10.1016/s0040-4020(01)96161-7
• 作为产物：
  描述：

  胆固醇杂质EPA 在 palladium on activated charcoal 、 Lindlar's catalyst 喹啉 、 sodium hydroxide 、 碳酸氢锂 、 pyridiniumchlorochromate on aluminumoxide 、 氢气 、 phenyltrimethylammonium tribromide 、 dipyridine chromium trioxide 、 lithium chloride 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 35.27h， 生成 5β-cholesta-1,7-diene-3,6-dione
  参考文献：
  名称：

  Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis in Locusta migratoria

  摘要：

  We have synthesized a tritiated form of 14-alpha-hydroxy-5-beta-cholest-7-ene-3,6-dione (5-beta-diketol) of high specific activity (1.74 TBq/mmol) from 7-dehydrocholesterol in seven steps with stereoselective introduction of the A/B cis ring junction as the key reaction. We have examined the ability of endocrine glands (prothoracic glands) of Locusta migratoria to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. A very efficient conversion of 5-beta-diketol to ecdysone and to 3-dehydroecdysone was monitored, which opens up new possibilities for the understanding of the role of 3-dehydro-compounds in ecdysteroid biosynthesis.

  DOI：

  10.1016/s0040-4020(01)96161-7