silenosterone | 74396-16-0

• 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: silenosterone
• 英文别名: 3-Dehydro-2-deoxyecdysone；(5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-1,2,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6-dione
• CAS: 74396-16-0
• 化学式: C₂₇H₄₂O₅
• 分子量: 446.627
• InChiKey: PDQPHVPWJVSDEA-IHTFJKPZSA-N

物化性质

• 沸点：
  613.5±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  silenosterone 生成 (5R,9R,10R,13R,14S,17R)-17-((1S,2R)-1,5-Dimethyl-2,5-bis-trimethylsilanyloxy-hexyl)-10,13-dimethyl-14-trimethylsilanyloxy-1,4,5,9,10,11,12,13,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthrene-3,6-dione
  参考文献：
  名称：

  Identification and metabolic fate of ovarian 22-adenosine monophosphoric ester of 2-deoxyecdysone in ovaries and eggs of an insect, locusta migratoria

  摘要：

  DOI：

  10.1016/s0040-4020(01)88689-0
• 作为产物：
  描述：

  (3S,5R,9R,10R,13R,17R)-17-[(2S,3R)-3,6-二羟基-6-甲基庚烷-2-基]-3,14-二羟基-10,13-二甲基-2,3,4,5,9,11,12,15,16,17-十氢-1H-环戊二烯并[a]菲-6-酮 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 水 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 54.67h， 生成 silenosterone
  参考文献：
  名称：

  Synthesis of silenosterone, an insect-molting hormone

  摘要：

  Silenosterone is synthesized in five steps: acetylation of 2-desoxy-alpha-ecdysone (1), saponification of 2-desoxy-alpha-ecdysone-3,22-diacetate (2) to the 22-monoacetate (3), and oxidation of the latter to a ketone (4) and its base hydrolysis (5). The structures of the compounds are confirmed by PMR, IR spectroscopy, and mass spectrometry.

  DOI：

  10.1007/bf02236295

文献信息

• Identification and metabolic fate of ovarian 22-adenosine monophosphoric ester of 2-deoxyecdysone in ovaries and eggs of an insect, locusta migratoria
  作者：Georges Tsoupras、Charles Hetru、Bang Luu、Emilia Constantin、Marie Lagueux、Jules Hoffmann

  DOI：10.1016/s0040-4020(01)88689-0

  日期：1983.1
• Synthesis of silenosterone, an insect-molting hormone
  作者：N. Z. Mamadalieva、N. Sh. Ramazanov、Z. Saatov

  DOI：10.1007/bf02236295

  日期：1999.11

  Silenosterone is synthesized in five steps: acetylation of 2-desoxy-alpha-ecdysone (1), saponification of 2-desoxy-alpha-ecdysone-3,22-diacetate (2) to the 22-monoacetate (3), and oxidation of the latter to a ketone (4) and its base hydrolysis (5). The structures of the compounds are confirmed by PMR, IR spectroscopy, and mass spectrometry.