(20R,20'R,22R,22'R)-2β,2'β,3β,3'β,20,20',22,22',25,25'-decahydroxy-[7αH,7'αH-bi(5β-cholest-8(14)-ene)]-6,6'-dione | 405509-14-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (20R,20'R,22R,22'R)-2β,2'β,3β,3'β,20,20',22,22',25,25'-decahydroxy-[7αH,7'αH-bi(5β-cholest-8(14)-ene)]-6,6'-dione
• 英文别名: 7αH,7'αH-bis[(20R,22R)-2β,3β,20,22,25-pentahydroxy-5β-cholest-8(14)-en-6-one-7-yl]；7,7'-bis-14-deoxy-8(14)-ene-20-hydroxyecdysone；(2S,3R,5R,7R,9R,10R,13R,17S)-7-[(2S,3R,5R,7R,9R,10R,13R,17S)-2,3-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-yl]-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
• CAS: 405509-14-0
• 化学式: C₅₄H₈₆O₁₂
• 分子量: 927.27
• InChiKey: CTFQTEYQLFVATF-GYGXBTFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  66
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  236
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (20R,20'R,22R,22'R)-2β,2'β,3β,3'β,20,20',22,22',25,25'-decahydroxy-[7αH,7'αH-bi(5β-cholest-8(14)-ene)]-6,6'-dione 在 吡啶 作用下， 生成 C₆₂H₉₄O₁₆
  参考文献：
  名称：

  Photochemical transformation of 20-hydroxyecdysone: production of monomeric and dimeric ecdysteroid analogues

  摘要：

  Structural modification of 20-hydroxyecdysone (20E) based on photochemical trans formation yielded dimeric ecdysteroid 7alphaH,7'alphaH-bis-[(20R,22R)-20,3p,2beta,3beta,20,22,25-pentahydroxy-5beta-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and t4-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the B-II-bioassay compared with the original 20E. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00140-4
• 作为产物：
  描述：

  蜕皮激素 以 水 为溶剂， 反应 4.0h， 以17%的产率得到(20R,20'R,22R,22'R)-2β,2'β,3β,3'β,20,20',22,22',25,25'-decahydroxy-[7αH,7'αH-bi(5β-cholest-8(14)-ene)]-6,6'-dione
  参考文献：
  名称：

  Dimeric Ecdysteroid Analogues and Their Interaction with the Drosophila Ecdysteroid Receptor

  摘要：

  三种结构相关的特定类似激素类衍生物，即14-去氧-8(14)-烯类20-羟基脱氧雄甾酮的7,7'-二聚体，通过光化学转化得到，分别为20-羟基脱氧雄甾酮、波纳斯特龙A和阿苏龙C。二聚体激素的结构主要通过核磁共振光谱学鉴定，辅以质谱和红外光谱。二聚体生成产物的产率取决于反应物浓度和光反应条件。惰性气氛支持高产率，而氧气氛完全阻止了二聚体的形成。与相关原始激素相比，在果蝇BII生物检测中，这三种二聚体保留了相当高的激素受体激动活性。

  DOI：

  10.1135/cccc20061229