(20R,22R)-14α-hydroperoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one | 92006-91-2

• 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: (20R,22R)-14α-hydroperoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one
• 英文别名: 2β,3β:20,22-diacetonide 14α-hydroperoxy-14-deoxy-20-hydroxyecdysone；14-desoxy-20-hydroxy-14α-hydroperoxyecdysone 2,3:20,22-diacetonide；2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-(20R,22R)-14α-hydroperoxy-5β-cholest-7-en-6-one；(1R,2R,4S,8R,10R,14S,17S,18R)-14-hydroperoxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one
• CAS: 92006-91-2
• 化学式: C₃₃H₅₂O₈
• 分子量: 576.771
• InChiKey: ABJCDYLVBKCQSC-APTIWFLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (20R,22R)-14α-hydroperoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one 在 二甲基硫 作用下， 以 氯仿 为溶剂， 生成 脱皮甾酮 2,3:20,22-二缩丙酮
  参考文献：
  名称：

  Lesma, Giordano; Nali, Micaela; Palmisano, Giovanni, Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 857 - 858

  摘要：

  DOI：
• 作为产物：
  描述：

  脱皮甾酮 2,3:20,22-二缩丙酮 在 氨 、 氧气 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (20R,22R)-14α-hydroperoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-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

• Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton
  作者：V. N. Odinokov、I. V. Galyautdinov、A. Sh. Ibragimova、N. A. Veskina、L. M. Khalilov、F. M. Dolgushin、Z. A. Starikova

  DOI：10.1007/s10593-008-0157-7

  日期：2008.9

  The reaction of ecdysteroids (20-hydroxyecdysone and its acetonides) with lithium in liquid ammonia gave novel analogs with an oxetane 9 alpha,14 alpha-oxacycle in the steroid skeleton. In aqueous alcohol solution the 9,14-oxa analogs rearrange to the more stable 9 alpha,13 alpha-oxa analogs through a 1,2-migration of the 18-Me group from the C-13 to the C-14 atom.
• Lesma, Giordano; Nali, Micaela; Palmisano, Giovanni, Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 857 - 858
  作者：Lesma, Giordano、Nali, Micaela、Palmisano, Giovanni、Tollari, Stefano

  DOI：——

  日期：——
• 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.
• Δ8(14)-14α-deoxy- and 14α-deoxy-14α-hydroperoxyecdysteroids
  作者：A. Sh. Ibragimova、N. A. Ves’kina、I. V. Galyautdinov、V. N. Odinokov

  DOI：10.1134/s1070428010110205

  日期：2010.11

  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.
• 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.