(20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-8(14)-en-6-one | 1161411-78-4

• 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: (20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-8(14)-en-6-one
• 英文别名: (20R,22R)-25-hydroxy-2β,3β:20,22-bis-(isopropylidenedioxy)-5β-cholest-8(14)-en-6-one
• CAS: 1161411-78-4
• 化学式: C₃₃H₅₂O₆
• 分子量: 544.772
• InChiKey: QLMGYAXMJSGOMF-FLYDNCENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-8(14)-en-6-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以74%的产率得到(20R,22R)-6β,25-dihydroxy-2β,3β:20,22-bis-(isopropylidenedioxy)-5α-cholest-8(14)-ene
  参考文献：
  名称：

  Δ8(14)-14α-deoxy- and 14α-deoxy-14α-hydroperoxyecdysteroids

  摘要：

  Delta(8(14))-14 alpha-deoxy-and 14 alpha-deoxy-14 alpha-hydroperoxyecdysteroids were synthesized, the reduction of Delta(8(14))-14 alpha-deoxy-20-hydroxyecdysone diacetonide at treatment with complex hydrides of alkali metals was investigated, and the stereochemistry of the obtained 6-hydroxy derivative and its acetate was established.

  DOI：

  10.1134/s1070428010110205
• 作为产物：
  描述：

  脱皮甾酮 2,3:20,22-二缩丙酮 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以58%的产率得到(20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-8(14)-en-6-one
  参考文献：
  名称：

  Δ8(14)-14α-deoxy- and 14α-deoxy-14α-hydroperoxyecdysteroids

  摘要：

  Delta(8(14))-14 alpha-deoxy-and 14 alpha-deoxy-14 alpha-hydroperoxyecdysteroids were synthesized, the reduction of Delta(8(14))-14 alpha-deoxy-20-hydroxyecdysone diacetonide at treatment with complex hydrides of alkali metals was investigated, and the stereochemistry of the obtained 6-hydroxy derivative and its acetate was established.

  DOI：

  10.1134/s1070428010110205

文献信息

• Unexpected formation of an oxetane cycle by oxidation of diacetonide of 20-hydroxyecdysone with oxygen in an alkaline medium
  作者：Victor N. Odinokov、Ilgiz V. Galyautdinov、Aliya Sh. Ibragimova、Natalya A. Veskina、Leonard M. Khalilov、Fedor M. Dolgushin、Zoya A. Starikova

  DOI：10.1016/j.mencom.2008.09.023

  日期：2008.9

  The diacetonides of 9 alpha,14 alpha-epoxy-14-deoxy-20-hydroxyecdysone and 14 alpha-hydroperoxy-14-deoxy-20-hydroxyecdysone have been obtained by the interaction of diacetonide of 20-hydroxyecdysone with a solution of lithium in liquid ammonia and following treatment with ammonia chloride and atmospheric oxygen.
• Synthesis of ecdysteroids with migrated group H3C 18
  作者：N. A. Ves’kina、V. N. Odinokov

  DOI：10.1134/s1070428011050162

  日期：2011.5

  Acid-catalyzed rearrangement of oxetane ring in oxetanoecdysteroids and their 7,8 alpha-dihydroanalogs made it possible to synthesize ecdysteroids with H3C18 group migrated from C-13 to C-14 atom.