14α-hydroxy-5β-cholest-7-ene-3,6-dione | 53296-90-5

• 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: 14α-hydroxy-5β-cholest-7-ene-3,6-dione
• 英文别名: 14alpha-Hydroxy-5beta-cholest-7-ene-3,6-dione；(5R,9R,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6-dione
• CAS: 53296-90-5
• 化学式: C₂₇H₄₂O₃
• 分子量: 414.629
• InChiKey: AJPPBYXIXOLGAV-QHKDMNIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  14α-hydroxy-5β-cholesta-1,7-diene-3,6-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以98%的产率得到14α-hydroxy-5β-cholest-7-ene-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

文献信息

• Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis in Locusta migratoria
  作者：F Dolle

  DOI：10.1016/s0040-4020(01)96161-7

  日期：1991.8.19

  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.