(3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-carbonitrile | 915159-30-7

• 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: (3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-carbonitrile
• CAS: 915159-30-7
• 化学式: C₃₁H₅₃NOSi
• 分子量: 483.853
• InChiKey: OCYJCBZNKBCNMM-AHURCFASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.29
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-carbonitrile 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.33h， 生成 (3α,8α,9β,10α,13α,14β,17α,20S)-25-hydroxycholesterol
  参考文献：
  名称：

  Synthesis of ent-25-hydroxycholesterol

  摘要：

  25-Hydroxycholesterol (25-HC) appears to play a role in several important biological processes, including regulating cellular cholesterol levels and promoting apoptosis. However, in most cases the mechanisms by which 25-HC elicits its biological effects are not known. Insights into mechanisms of 25-HC action can be gained by studying the activity of its enantiomer (ent-25-HC). ent-25-HC is physically and chemically identical to 25-HC; however, 25-HC and ent-25-HC can be distinguished in chiral environments, like a protein binding site. In order to probe the mechanisms of 25-HC action, we have synthesized the enantiomer of 25-HC (ent-25-HC). (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.007
• 作为产物：
  描述：

  (3α,8α,9β,10α,13α,14β,17α,20S)-chol-5-en-24-oic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 52.0h， 生成 (3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-carbonitrile
  参考文献：
  名称：

  Synthesis of ent-25-hydroxycholesterol

  摘要：

  25-Hydroxycholesterol (25-HC) appears to play a role in several important biological processes, including regulating cellular cholesterol levels and promoting apoptosis. However, in most cases the mechanisms by which 25-HC elicits its biological effects are not known. Insights into mechanisms of 25-HC action can be gained by studying the activity of its enantiomer (ent-25-HC). ent-25-HC is physically and chemically identical to 25-HC; however, 25-HC and ent-25-HC can be distinguished in chiral environments, like a protein binding site. In order to probe the mechanisms of 25-HC action, we have synthesized the enantiomer of 25-HC (ent-25-HC). (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.007