14alpha-Deoxy-20-hydroxyecdysone

• 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: 14alpha-Deoxy-20-hydroxyecdysone
• 英文别名: (20R,22R)-2β,3β,20,22,25-pentahydroxy-5β-cholest-7-en-6-one；14α-Deoxy-20α-hydroxyecdysone；14α-deoxy-20-hydroxyecdysone；14-deoxy-20-hydroxyecdysone；alpha-14-deoxy-ecdysterone；(20r,22r)-2beta,3beta,20,22,25-Pentahydroxy-5beta-cholesta-7-en-6-one；(2S,3R,5R,9R,10R,13S,14R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
• 化学式: C₂₇H₄₄O₆
• 分子量: 464.643
• InChiKey: KBDUJCBPMFPAJU-JGXAIIDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  蜕皮激素 以 水 为溶剂， 反应 4.0h， 以1 mg的产率得到(1R,5R,7R,8S,10R,11R,14S,15S)-7,8-dihydroxy-10-methyl-15-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]pentacyclo[12.3.1.01,14.02,11.05,10]octadec-2-en-4-one
  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

文献信息

• Fe(II)-Induced Fragmentation Reaction of ?-Hydroperoxy-?,?-enones. Part 1. Synthesis of 13(14?8)-abeo-Steroids
  作者：Luigi Canonica?、Bruno Danieli、Giordano Lesma、Giovanni Palmisano、Angelo Mugnoli

  DOI：10.1002/hlca.19870700320

  日期：1987.5.6

  Some steroidal analogues embodying the hitherto unknown 13(148)-abeo skeleton have been synthesized by Fe(II)-induced rearrangement (tandem β-fission/reductive alkylation) of 14α-hydroperoxy-7-en-6-ones. The configurational assignment was made by thorough analysis of NMR spectra; the structure of one of the products was unambiguously assessed by X-ray single-crystal analysis.

  通过Fe（II）诱导的14α-hydroperoxy-7-en-6-one的重排（串联β-裂变/还原烷基化）合成了一些体现迄今未知的13（148）-abeo骨架的甾体类似物。通过对NMR光谱的彻底分析来进行构型分配。通过X射线单晶分析明确评估了其中一种产品的结构。
• Unusual photochemical behaviour of the enone chromophore of the insect moulting hormone 20α-hydroxyecdysone
  作者：Luigi Canonica、Bruno Danieli、Giordano Lesma、Giovanni Palmisano

  DOI：10.1039/c39850001321

  日期：——

  U.v. irradiation of the most representative insect moulting hormone 20α-hydroxyecdysone (1) in follows two unusual pathways the reduction products (2) and (4)(path a) together with the ketone (5) and the cyclobutanol(6)(path b).

  最有代表性的昆虫蜕皮激素20的UV照射α -hydroxyecdysone（1）在遵循两个不同寻常的途径中的还原产物（2）和（4）（路径）与酮（一起5）和环丁醇（6）（路径b）。
• Photochemical transformation of 20-hydroxyecdysone: production of monomeric and dimeric ecdysteroid analogues
  作者：Juraj Harmatha、Miloš Buděšínský、Karel Vokáč

  DOI：10.1016/s0039-128x(01)00140-4

  日期：2002.2

  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.