5β-cholesta-1,7-dien-3-one | 137204-83-2

• 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-dien-3-one
• 英文别名: (5R,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4,5,6,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 137204-83-2
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: PZMMQWPKNDDCII-GFWJTQLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 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：
  0.81
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5β-cholesta-1,7-dien-3-one 在 dipyridine chromium trioxide 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以27%的产率得到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：

  胆甾-4,7-二烯-3-酮 在 palladium on activated charcoal sodium hydroxide 、 碳酸氢锂 、 氢气 、 phenyltrimethylammonium tribromide 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 5β-cholesta-1,7-dien-3-one
  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