(5α,8α,9β,10α,13α,14β,17α,20S)-cholestan-3-one | 1325206-96-9

• 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: (5α,8α,9β,10α,13α,14β,17α,20S)-cholestan-3-one
• 英文别名: ent-coprostanone
• CAS: 1325206-96-9
• 化学式: C₂₇H₄₆O
• 分子量: 386.662
• InChiKey: PESKGJQREUXSRR-SROJHNJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (5α,8α,9β,10α,13α,14β,17α,20S)-cholestan-3-one 在 氨 、 pyridinium hydrobromide perbromide 、 lithium 、 potassium tri-sec-butyl-borohydride 、 lithium chloride 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 10.25h， 生成 (3β,4β,5β,8α,9β,10α,13α,14β,17α,20S)-4-(2-propenyl)cholestan-3-ol
  参考文献：
  名称：

  Synthesis of the enantiomer of the oxysterol-antagonist LY295427

  摘要：

  Cellular cholesterol homeostasis is regulated by oxygenated cholesterol metabolites called oxysterols. While the importance of oxysterols in the acute regulation of cholesterol homeostasis is known, the precise molecular mechanisms through which oxysterols exert their effects remain to be elucidated. LY295427 (1) is a known antagonist of the cholesterol-homeostatic effects of 25-hydroxycholesterol (25-HC), a biologically active oxysterol. In order to examine the mechanism of action of this antagonism, and to further explore recent evidence suggesting that the membrane effects of 25-HC contribute to acute cholesterol regulation, we synthesized the enantiomer of LY295427 (ent-LY295427). ent-LY295427 (2) will serve as a unique probe to provide insight into the role of transcription-independent mechanisms in regulation of cholesterol homeostasis. Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2011.03.008
• 作为产物：
  描述：

  (3β,5α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cholest-24-ene 在 Jones reagent 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 24.5h， 生成 (5α,8α,9β,10α,13α,14β,17α,20S)-cholestan-3-one
  参考文献：
  名称：

  Synthesis of the enantiomer of the oxysterol-antagonist LY295427

  摘要：

  Cellular cholesterol homeostasis is regulated by oxygenated cholesterol metabolites called oxysterols. While the importance of oxysterols in the acute regulation of cholesterol homeostasis is known, the precise molecular mechanisms through which oxysterols exert their effects remain to be elucidated. LY295427 (1) is a known antagonist of the cholesterol-homeostatic effects of 25-hydroxycholesterol (25-HC), a biologically active oxysterol. In order to examine the mechanism of action of this antagonism, and to further explore recent evidence suggesting that the membrane effects of 25-HC contribute to acute cholesterol regulation, we synthesized the enantiomer of LY295427 (ent-LY295427). ent-LY295427 (2) will serve as a unique probe to provide insight into the role of transcription-independent mechanisms in regulation of cholesterol homeostasis. Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2011.03.008