(1S)-1-[4-(tert-butyldiphenylsilanyloxymethyl)phenyl]-2-oxiranyl-ethanol | 475160-78-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S)-1-[4-(tert-butyldiphenylsilanyloxymethyl)phenyl]-2-oxiranyl-ethanol
• 英文别名: (1S)-1-[4-[[tert-butyl(diphenyl)silyl]oxymethyl]phenyl]-2-[(2R)-oxiran-2-yl]ethanol
• CAS: 475160-78-2
• 化学式: C₂₇H₃₂O₃Si
• 分子量: 432.635
• InChiKey: SWPOIPDBRJGXMQ-BVAGGSTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-[4-(tert-butyldiphenylsilanyloxymethyl)phenyl]-2-oxiranyl-ethanol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以77%的产率得到(1S)-1-(4-hydroxymethylphenyl)-2-oxiranyl-ethanol
  参考文献：
  名称：

  Synthesis of 7200 Small Molecules Based on a Substructural Analysis of the Histone Deacetylase Inhibitors Trichostatin and Trapoxin

  摘要：

  [GRAPHICS]Seventy-two hundred potential inhibitors of the histone deacetylase (HDAC) enzyme family, based on a 1,3-dioxane diversity structure, were synthesized on polystyrene macrobeads. The compounds were arrayed for biological assays in a "one bead-one stock solution" format. Metal-chelating functional groups were used to direct the 1,3-dioxanes to HDAC enzymes, which are zinc hydrolases. Representative structures from this library were tested for inhibitory activity and the 1,3-dioxane structure was shown to be compatible with HDAC inhibition.

  DOI：

  10.1021/ol016915f
• 作为产物：
  描述：

  对苯二甲醇 在 tris(triphenylphosphine)ruthenium(II) chloride 咪唑 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 Pseudomonas cepacia lipase 、 vanadyl acetylacetonate 、 potassium tert-butylate 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 赤霉素 、 N,N-二异丙基乙胺 、 potassium iodide 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 、 正丁醇 为溶剂， 反应 105.97h， 生成 (1S)-1-[4-(tert-butyldiphenylsilanyloxymethyl)phenyl]-2-oxiranyl-ethanol
  参考文献：
  名称：

  Synthesis of 7200 Small Molecules Based on a Substructural Analysis of the Histone Deacetylase Inhibitors Trichostatin and Trapoxin

  摘要：

  [GRAPHICS]Seventy-two hundred potential inhibitors of the histone deacetylase (HDAC) enzyme family, based on a 1,3-dioxane diversity structure, were synthesized on polystyrene macrobeads. The compounds were arrayed for biological assays in a "one bead-one stock solution" format. Metal-chelating functional groups were used to direct the 1,3-dioxanes to HDAC enzymes, which are zinc hydrolases. Representative structures from this library were tested for inhibitory activity and the 1,3-dioxane structure was shown to be compatible with HDAC inhibition.

  DOI：

  10.1021/ol016915f